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Views: 250 Created: 5 months ago Updated: 5 months ago

The Caretaker- Jenn returns

The letter

I awoke Monday morning feeling great. A good night sleep had done wonders and my episode with Jenn administering two enemas the previous afternoon no doubt helped immensely. I heard Mrs. G or perhaps Jenn downstairs taking care of the horses as Jenn said they would. So I took the opportunity to have coffee and watch the news and weather. Finishing the coffee I headed down to the barn where I found Jenn finishing up with the chores.

"Good morning Jenn, thanks for taking care of the chores this morning."

"Good morning and you're welcome. All rested up?" Jenn replied.

"Yes I am, feel much better. Needed a night to catch up."

"Great. So Mother and I will be leaving soon unfortunately. We do enjoy our time here away from the city. We will be in contact as to when we will be back up. The place looks great and we both thank you for that. I need to get packed and get on the road. So enjoy the day and I will see you in a few weeks. Bye now."

"Ok Jenn, sounds good, have a safe drive, good bye."

A few days later I found a letter in the mail. From Jenn. I took it upstairs sitting down to see what she had to say.

Dear Tim,

I want to share some thoughts with you. First, thank you for your cooperation last Sunday. No arguments, just doing as asked. It was very much appreciated. Next, thank you for your honesty. I'm sure admitting that you have found you enjoyed the "procedure" was not easy. Though it did take a bit of coaxing on my part. And again you were honest in admitting that getting spanked was also enjoyable, at least if it's not Mother's strap. It took some courage to admit to that I am sure.

And now some honesty from me. I told you there was no need to be embarrassed about enjoying enemas and that I myself use them occasionally both to relieve constipation, but sometimes just because it feels good. Something I did not share was how much I delight in giving enemas, especially to someone like yourself. (Is that naughty of me? LOL!) I have to admit I have looked more than once at your bottom as you were working, thinking how exciting it would be to give you enemas. And having had the opportunity to do so I was absolutely correct. Helping you to release about put me over the edge. My little secret? Later that evening I thought about our encounter and brought myself to a wonderful orgasm while I envisioned slipping the enema nozzle in your sexy butt. And I could not have wrapped up the afternoon any better than putting you over my knee, as you requested, and spanking your bottom. I honestly do not know how I was able to keep from getting myself off immediately it was so arousing for me.

So now you know. We both have similar interests in regard to this.

Hon, I hope you are not put off by my confession. If so, please tell me. While I can not control my mother's actions I can control my own. So we may find we are ordered to comply with her demands, but I will not place any demands of my own upon you regarding enemas or spanking. However, as I made clear last Sunday I am quite willing to administer both enemas and a spanking if you wish. Another little secret between us. (We seem to be developing quite a list of "little secrets" to keep from Mother, are we not?) If you are amenable to continuing our secret no need to respond. On the other hand, if you find this unacceptable, send me a reply. Can you guess that I am hoping not to hear from you?

One final thing. I gave you the choice of what position you would like to be in to receive your second enema. Your choice of going over my knee was wonderful. I loved the feel of having you in such a position. The closeness and the intimacy as you allowed me to give you the enema was fantastic. While having you OTK it came to me how much I would like to give you an enema using a bulb syringe. No doubt how you received an enema as a baby. So, assuming I will not receive a response saying no more, I am sending another gift. A bulb syringe for enemas. I ask that upon receiving it you put it away, do NOT use! I am being selfish, I want to be the first to administer a bulb enema to you!

I plan on being up again in a few weeks, actually trying to find a week end that Mother will not be be in attendance. Now why in the world would I want that? Any idea? I imagine you do. Very much looking forward to my next trip to the property.


PS- This letter will not self destruct after reading (Like in Mission Impossible I believe?) so perhaps it needs to be burned rather than thrown away? More mystique that way? LOL!


Quite the admission I thought. And one that I could have only dreamed of. Certainly wasn't a difficult decision as to whether to respond. Nope, Jenn would receive no response and I would try my best to stash that enema bulb until Jenn's next arrival. I hope it's soon. But then, there is no reason I can not use what Jenn sent previously. With a smile I headed for the bathroom to prepare.


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