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Views: 404 Created: 5 months ago Updated: 5 months ago

The Caretaker- Jenn returns

Chapter Three

Thoughts raced through my mind. I was not expecting this. A part of me was thinking I do not want this again. It's embarrassing and even a little humiliating to be not only exposed to Jenn, but then having her take my temperature as if I were a small child.. A thermometer inserted into my rear followed by an enema. But on the other hand???

I hesitated then spoke. "Jenn, I'm just really tired, I just need a little rest."

"And rest you will get right after we have done what Mother has asked. I am not sure why this is seeming to be a problem. Let me ask this. Did you ever get an enema growing up?"

"Maybe when I was a baby, but other than that no."

"So my mother gave you your first enemas? As you may recall she shared with me in detail what took place. You received two enemas each time for part of your consequences for your actions. After that you took it upon yourself to search out and borrow the enema equipment. So did you borrow it because you didn't feel well? Because you were constipated?"

"No , neither," I replied.

"So that being the case, why would you want an enema? Unless, of course, you found you liked it? It would seem to be the case in this instance. Am I missing something? Have you found you like getting an enema?"

I felt myself blush, I shrugged my shoulders feeling like a deer caught in the headlights.

"There is no need to be embarrassed. I do enemas once in awhile when I'm feeling backed up and sometimes just because I enjoy the feeling and pleasure I get from an enema. OK? So be honest. I think you have discovered the same. Do you like getting an enema?"

I felt myself blush again as I nodded, "Yes I guess I do."

"It's kind of a Catch 22 thing is it not? Something that doesn't quite make sense. Parts that can certainly be embarrassing and uncomfortable, but also at the same time one finds some bit of pleasure. So let's continue, get undressed as I asked."

I pulled my Tshirt off and felt myself becoming erect as I dropped my jeans and underwear as Jenn applied vaseline to the thermometer. I lay down finding comfort in Jenn's words regarding what was about to take place. I took a deep breath and exhaled. Anxiety had disappeared and I was fully ready to experience again what was about to take place. Jenn sat the edge of the bed next to me.

"I need you to spread your legs a little please. Yes, that's good."

I felt my bottom separated and the thermometer slipped in place. I emitted a slight sigh, the sensation feeling so good added to the fact I was so exposed led to that Catch 22 thing. Embarrassed, but somehow liking it. Jenn held the thermometer in place while massaging my back gently. After a minute she began to slide the thermometer in and out causing another sigh of pleasure.

"Feels good doesn't it? And it is going to feel even better when I give you your enema." She removed the thermometer. "Normal temp, that's good. I'm going to prepare your enema now."

I listened as Jenn made the preparations. You are getting an enema I thought. An enema. Jenn will order me into whatever position she desires. Then she will be free to see me completely exposed, my bottom hole on full display. Again feeling some embarrassment but loving the feeling of being so vulnerable. I felt myself harden knowing what was coming. Jenn entered full bag in hand, and hung it from the stand. I watched as she lubed the nozzle. Not the larger douche nozzle this time, just the smaller straight nozzle.

"Ok, spread your legs for me again," as she sat once more at the edge of the bed. Her hand separated my bottom and the nozzle inserted. "Enema time," and she opened the clamp allowing the flow of the enema.I relaxed fully as the warm, soapy water began to fill me. It felt so good. No more feeling embarrassed, but overcome with pleasure of a nozzle and the enema it delivered.

"You are doing well taking your enema. You feeling ok?"

"Yes, I'm fine. It does feel good." I admitted. Just then I heard the entrance door open and close. Then footsteps coming upstairs. I began to panic. Someone was coming and I didn't want to be caught in this position. "Jenn. Someone is here."

"It's just Mother. She said she would be up to check on how things were going. Now just relax and take your enema." There was light knock on the door before it opened and Mrs. G entered. Another flash of embarrassment flooded over me as she came into the bedroom to observe seeing me naked with an enema hose protruding from my backside.

"Sorry for my intrusion, but I wanted to see how things are going. Any fever Jenn?"

"None at all Mom, completely normal. And our patient has been very cooperative with both having his temp taken and allowing me to give him his enema."

"I think you should give him another after this. A thorough clean out can not hurt."

The enema was working as I looked at the bag now three quarters empty. I was feeling quite full and the flow seemed to have slowed. "Jenn, I'm starting to get uncomfortable. I don't think its going in anymore."

"I think you're right. So keep your head down but up on your knees, see if we can't get the rest of your enema in."

I did as told somewhat reluctantly knowing I was exposing my excitement. The enema began to flow once more and my erection surged. Neither lady made a comment which would surely cause more embarrassment. Within a few minutes I heard the gurgle as the bag emptied completely. Jenn did not make me wait. She removed the nozzle. "Go use the bathroom."

I hurried off to expel hearing Mrs. G, "It looks like you have things well in hand so I will get back to other matters. Give him a second enema and I will see you when you are finished." With that she exited.

The initial release was over and I sat waiting for the next feeling knowing it was coming which it soon did. For a few minutes it seemed it would never end. When it did I felt relieved but exhausted. I went to the sink and cleaned myself before presenting myself to Jenn.

My erection had subsided thankfully as I stood before her. The enema bag had been refilled.

"So since this is not for punishment I thought I would let you decide how you want this next enema. Your choice. Lying down, or head down bottom up as we just did or on your back, up to you. Which would you prefer?"

I wasn't expecting a choice, but given it I quickly decided. "Ah, do you think maybe, ah, maybe I could be over your lap like a spanking but for the enema instead?"

"Hon if that's what you would like that is what we will do." She sat on the bed arranging a towel over her lap. "There now, over you go." She helped me ease over her lap into position. A few moments later the nozzle was inserted and the enema released. Immediately I felt myself stiffen.

"My what is that? What's that old movie line? Is that a gun or are you just happy to see me?"

"I'm sorry Jenn, I can't help it."

"No need to apologize, of course you can't help it. It's a natural reaction. Just relax and enjoy."

Without thinking or meaning to I began to push against her lap seeking relief.

"Naughty boy what are you up to?" her hand landed with a sharp snap across my bare bottom which only caused me to press against her lap further.I heard the click as the clamp closed shutting off the flow and the nozzle was removed.

"Stand up for me." I did so with my erection at its full. "Look at you, so excited. She stood and placed the towel on the bed. " Now naughty boy lie down on your back and lift your legs up so I can restart your enema and see if I can't help out."

I did as directed and with legs up Jenn inserted the nozzle and began the flow. Looking at me with a smile she grasped my erection. "I think you need a release in addition to your enema." She began to stroke my hardness and with the feeling of a nozzle inside, warm water flowing and being so exposed it was not long before I began to build to a climax.

"Jenn, you're going to make me cum. I can't stop it."

"Let it go sweetie, make a big cum for me." as she slid the nozzle in and out. I hit the point of no return. I felt the pressure build slowly becoming more intense by the second. I rode a wave of pleasure for half a minute before I jerked convulsively in orgasm. Had I ever cum so hard before? It seemed I was about to pass out.

"Good boy, you had so much to release." Jenn gave me a sweet smile. She closed the clamp. Go to the bathroom now."

I did as I was told feeling a little weak in the knees from the orgasm. As before I released the enema and got myself cleaned up and left the bathroom. Jenn had cleaned the gear and was placing it back in the box.

"Feeling better?"

"Yes, definitely Jenn. Thank you."

"Great. Now obviously a bit of what happened will remain between us. Mother need not know all details. No lies, just not the whole story if you know what I mean?"

"Yes, of course. I get it."

"Let me ask. Did you enjoy the last hour or so? Did you like me giving you your enema or do you like it better by doing it yourself?"

"I guess I prefer getting it from you, it's easier for sure. And when you, you know, did the other thing it was really exciting. No one has ever done that like you."

"Well, I will keep that in mind. Now if you, in the future, want or need an enema, and I am around just ask. I will be happy to oblige you. Another secret we keep from Mother. No need for her to know you have come to like enemas. And she will believe she is applying punishment when instead you are enjoying it. Doesn't save you from the strap however, and I know that can not be pleasant. Nothing like a little over the knee spanking at all, wouldn't you agree?"

"The strap is awful, it hurts, bad and Mrs. G isn't shy when she applies it for sure." I thought back about those two strappings and the spanking Jenn gave me. No comparison at all. Actually thinking back- should I tell her" Could I just ask? I think I could and I think she might be ok with it. Why not? Tell her now, never a better opportunity to share such thoughts.

"Ah Jenn, I want to tell you something, Ok?"

"Of course it's ok, what is it?" It's kind of embarrassing, actually a lot embarrassing. But, well, I kind of liked it when you spanked me. I mean it hurt and all, but not like the strap."

"Really now? Quite interesting. So I see where this is going. So I think you need to ask me please."

"Ask you?"

"Yes, ask me. Jenn, will you please spank me because I am naughty? Go ahead, ask."

Well you got yourself into this I thought. Looking down at the floor I said quietly, "Jenn will you please spank because I am naughty?"

"How can I not when you ask so nicely." Jenn went to the drawer of kitchen utensils pulling out the large spatula. Turning she took my hand leading me to the couch where she sat down. "Over my knee young man, I am going to spank your bare bottom red. Give you the spanking you asked for."

Still naked I lay over her lap knowing what was coming. I felt the spatula caressing my bottom, "Naughty naughty boy I have here. Having to spank you like this." With that she began to spank, no warm up just hard spanks of the spatula reminding me of seeing a neighbor spank her daughter's bare ass with a similar utensil. It landed over and over across my bottom, one cheek then the other, then both. "You so need this and I am happy to be the one to give it. She spanked harder and faster until I was squirming and sobbing, my bottom surely red as she said it would be.

She stopped. "OK, almost finished. Get ready, 25 more very very hard. Give me your right hand."

I put my hand behind me which she held firmly as she draped a leg over mine pinning me in place. I lay in place waiting, but not for long. The spatula landed with a sharp crack. Then Jenn went full force the spatula landing twenty-five times on my already red bottom. I had had enough, as tears filled my eyes.

"There all over sweetie, get up."

I did so and Jenn took my hand, "Sit here," patting her lap. I sat down gingerly and Jenn gave me hug and rubbed my bottom. "There now, all better. We have had quite the time haven't we? And you are a delight to be so intimate with. Give me hug and I will be on my way to report to Mother all is well. And the spanking will be another secret of ours. A quick peck on the cheek and a hug and Jenn left.

If she would have come back a few minutes later she would have found me naughty again as I masturbated with the red bottom and thinking of being OTK with her again in the future.

The End (At least for now)

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