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Views: 380 Created: 7 months ago Updated: 7 months ago

The Caretaker- Over My Head

Chapter Four

Upstairs I spent a half hour relieving myself before cleaning up. After showering I took a moment to look over my shoulder in the mirror to see a still very red bottom. I pulled on a Tshirt and a pair of clean jeans and sat with a coffee to browse through a magazine before I going for a walk to check the property.

Back upstairs the phone rang. "Hi, it's Jenn. I will be over in a few minutes. How are you feeling?"

"I'm ok, ah, unless-" I began to reply.

"No need to explain, I understand, I will be over shortly."

She is coming over to give you another enema I thought. What can I expect this time? The bulb enema was fantastic. Such a difference from receiving from the bag. While the bag gave a constant gentle flow the bulb could be squeezed to give a jet of soapy water. Then the repeated infiltration of the nozzle in and out of my bottom was pure pleasure. It was quite hard to believe the sensation of the nozzle being inserted and removed could be so arousing. I found myself pacing around the apartment while I awaited Jenn's arrival.

A few minutes later I met Jenn at the door. "Hey Jenn," I noticed she carried a small bag which she set down next to her on the couch.

"Hello again, come here please."

I stepped over to stand before Jenn. She reached out taking my hands in hers as she looked up at me.

"You know I was thinking I would offer you the choice of whether to receive another enema, but after further thought I decided against that. Why you might ask? Because- just because I want to. So please take off your shirt."

She released my hands so I could do as asked. I pulled off my shirt. "Ok, now your pants. Get them off please."

I did as she asked dropping my jeans and stepping out of them. She reached out to take my hands once more.

"I'm going to give you an enema."

I nodded in assent as I felt myself stiffening. It did not go unnoticed by Jenn

."Look at you. Enema! Does hearing that excite you? Does hearing me tell you I am going to give you an enema turns you on? It seems that is the case."

There was no hiding the fact, yes it did. Each time she said enema I got more aroused. By now I was fully aroused standing naked before Jenn knowing what was to come, at least to some extent. I watched as Jenn opened her bag to remove a rectal thermometer and the Vaseline along with latex gloves and a small bottle of skin lotion.

"Ok sweetie, over my lap so I can check your temp. I placed myself over her lap and a few seconds later the thermometer was inserted. Again the feeling of pleasure washed over me. The feeling of something in my rectum and the comfort feeling of lying over her lap as if a were a child being taken care of added to the pleasure.

"You have quite the red bottom. Let's apply some lotion shall we?"

So with a thermometer in my butt Jenn gently applied the lotion to my still burning bottom. The cool lotion added another level of pleasure. A few minutes later I felt the thermometer removed. Your temp is normal, that's good. Time for your enema. Please get up and would you get the enema bag for me please? And a couple of towels as well.

"I did as she asked retrieving both the enema gear and the towels

."I want you to place a towel on the floor in front of the couch please."

I did as she directed laying out a towel on the floor as she prepared the next enema. I also retrieved cymbol stand that served as a holder for the bag. I watched as she filled the bag and then swished a bar of ivory soap in the open top bag. Jenn hung the bag and ordered me to the floor. She sat on the couch and I watched as she pulled on a latex glove and dipped a finger into the Vaseline.

"Head down and bottom up please. Now you need to relax hon. Let me take care of you."

With that Jenn separated my bottom cheeks applying the lube to my opening gently massaging the area before slipping her finger inside me to its full extent. I moaned as her finger began to slide in and out causing another erection almost immediately. Damn, this woman is amazing I thought as she continued to finger my ass. With a deep breath I sighed relishing what this woman was doing. Her finger withdrew. I waited knowing what was next.

"Are you ready for your enema? Because I am ready to give you one. Tell me. Are you ready?"

"Yes Jenn."

"Good boy. Now ask. Jenn, would you please give me an enema?" It was obvious that she knew hearing or saying the word enema was extremely arousing for me and was putting that knowledge to good use.

"Jenn, would you please give me an enema?"

"What is it you want?"

Those butterflies again and the embarrassment of asking for an enema kicked in. "I, ah, I want an enema."

"Then let's give you one." Jenn held the douche nozzle if front of me. "This is going up your bare bottom to give you just what you want and need. Another good, soapy enema to wash you out. An enema just for you. And to think you have to bare your bottom to me just like if you were a little boy. So I can give you your enema."

Once again I felt my bottom separated as Jenn gently inserted the nozzle. Then the click followed by a rush of cool water turning warm as the enema flowed into my bottom. i was fully hard again.

"Did you play with yourself after your enema this morning? Be honest, I will not be upset if you did."

"No Jenn, I didn't honestly."

"You are sure? No fibbing?"

"No, I'm not fibbing. I didn't, really." I had thought about it, but knowing that I would be getting another enema gave me the idea I should wait. Only because I thought I would get off to a greater degree if I waited for the second enema.

"Ok I believe you. Will you masterbate after this one?" The answer was obviously yes, but embarrassing to admit.

"Ah, I don't know. maybe."

"Just maybe? Ok, though I believe I it is more than a maybe. Perhaps I can help with that decision." She began to slowly slide the douche nozzle in and out. Out to the point it was barely inside me then slid in its entire length and back out again all the while the enema flowed filling me. I felt like I could ejaculate in seconds given the opportunity.

Jenn's hand rubbed my bottom, then rubbed my back as she continued. Then back to my bottom sliding down to caress my balls as the enema continued. I was feeling full when Jenn whispered, "You have taken almost all of your enema, just a bit more."

A few minutes later the water stopped and the clamp was closed. Jenn slipped the nozzle out.

"Use the bathroom sweetie." and so I spent another 20-30 minutes releasing the enema. A relief as I cleaned up and returned to Jenn.

"All finished?" she asked. Over here, back on the towel, but just kneel down for me." I did so as Jenn watched.

"So you had two enemas. Do I need to give you another? Another enema?"

Each time the word enema was spoken it aroused me to an erection.

"My lord, enema certainly has quite the effect on you doesn't it? I want you to lay down on the towel, on your side facing me. Yes, that's good. Now masterbate for me. I want to watch. .

I looked at her with a bit of a shock. Really, play with myself in front of her? Just the thought aroused me further.

"Go ahead, it's ok. Show me."

I reached down to grasp my erection and began to stroke. This would not last long.

"Yes just like that," Jenn urged, "Don't stop, cum for me. Or I will have to give an enema again. Another enema!"

That word again. It put me over the top and within seconds the pressure built until I released feeling like I was being turned inside out. Breathing hard I spattered on the towel feeling drained.

"Good boy, such a big cum for me. And for you. Come with me."

Jenn led to the bathroom where she ran a washcloth under the hot water and then used it to clean me, gently washing my privates. Heaven! Finished we sat on the couch me still fully naked.

"How are you feeling?" Jenn said with a smile.

"I guess it's ok to say I feel good now? Actually I feel like I am melting. That was pretty incredible."

" I should hope you feel good after that. You know yesterday I said I was "talking" over your head. You did not catch on to where I was trying to take you. And today I can't help but wonder? Did you feel you were "in" over your head with what happened? That just occurred to me. Going from not understanding to understanding full well what was going on and thinking what on earth did I get myself into? Kind of funny don't you think? Anyway, now I will be on my way. I am feeling the need to feel good as well if you know what I mean? Giving you enemas is quite the turn on for both of us. And I need to relieve myself so to speak. So a big hug and good night. And thank you for catching on. It has been a delight.

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