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The Caretaker- Over My Head

Chapter Three

I took a deep breath as I slipped off the robe. Jenn sat smiling as I literally disrobed. The butterflies again as I hung the robe and turned to face her. I was getting hard as she patted her lap.

"My, getting so excited to get his enema this morning I see. Over you go." Jenn helped to ease me over her lap. "I need you over a bit further so your bottom is up, that's it. Good boy. Are you ready?"

"Jenn what if I have to go in a hurry?"

"If you don't think you can make it upstairs you can run into a stall. It wouldn't be a first. But I am not planning on filling you to bursting, just enough to help clean you out so you should be fine to get upstairs.

I hope so I thought as I flashed back to my punishment from Mrs. G when she caught me smoking. I was taken down to the barn where bent over a few hay bales with pants completely removed she strapped my bare ass. Then proceeded to give me a high volume enema in the stall making me expel there in front of her.

"Now relax and let me give you your enema." I felt my cheeks separated and Vaseline applied. I turned to watch as Jenn inserted the bulb into the soapy water squeezing out the air allowing the bulb to fill. Once again my bottom separated and the nozzle slipped in perhaps only an inch before I felt the warm water flow. Slowly the bulb emptied to be refilled. Jenn inserted the nozzle as before barely entering my rectum but this time she squeezed the bulb forcefully the water surging into me in a rush washing over my prostate. I felt my erection surge. The bulb emptied and was refilled. I felt Jenn slip the nozzle inside me that little bit and with a gentle squeeze the soapy water entered again, then I felt the nozzle go deep as Jenn again gave the bulb a powerful squeeze jetting the water into my insides in a rush.

I moaned with the pleasure of the sensation and my erection pressing against Jenn's lap. I began to thrust slightly. A sharp slap landed across my cheeks.

"Oh, don't you dare do that, don't you dare. You lie still and take your enema. No, instead lie still." She reached over to the stand picking up the hairbrush. "Lie still while I spank your naughty bottom."

Without any warm up Jenn began to apply the brush both forcefully and rapidly covering every inch of my exposed rear.

It came so unexpected I was caught off guard. I quickly began to wiggle and squirm. "Owww, stop, oww please? I'm sorry."

It stopped as soon as it started. "Ssshh, stop that and hold still." Jenn commanded as she draped a leg over mine locking me in place. "I think you need your bare bottom spanked as much as you need an enema. And now little man that is just what you are going to get."

The brush fell swiftly with force and within a minute I found my self sobbing, crying as the brush snapped against my bottom. I gave in to the spanking and lay limp across her lap crying as she continued. After another minute or so it stopped.

"Are you ready to behave now so I can continue your enema?" Jenn asked as she placed the brush back on the stand.

Looking over my shoulder, "Yes Jenn, I am sorry."

"Then let us finish a few more bulbs and we are done."

The enema began once more and I took the final bulbs before Jenn announced it was finished. "You may get up now. Can you make it upstairs?

"I think I can if I hurry."

"Come here then, give me a hug and get upstairs. And, we are not finished. I have a few things to attend to and it will give you some time to recuperate. But I will be over to administer another enema later. Do you understand?"

"Yes Jenn," and with a brief hug I hurried upstairs to the bathroom.