from Joanne

Dear Helga,

My plans for Paulina last night included the introduction to my new strapless strap-on as I felt it was time to take the next steps with her. Just to set the mood before dinner I had to her help get me out of my work attire as usual. This time I had her go get the strap-on then as a test have her insert it in my vagina. It actually is a unique design making it easy to hold in there. Of course I asked her what she thought of my new penis. After a few moves to ensure it was going to work I had Paulina remove it slowly then lick it all off. I do love to tease her so much Helga.

Later on after dinner and closer to bedtime Paulina gave me my nightly bath after a nice long drink of my nectar. I think she is starting to enjoy it Helga as she doesn't make a face or say anything now which is nice. I do admire Paulina for being able to drink and swallow without getting nectar all over her face.

At bedtime once again I had Paulina go get the strap-on then insert it in my vagina. Next I gave her a condom to slide down the dildo then handed her the lube to prepare the strap-on. Helga that has to be a scary feeling preparing a strap-on to be used on yourself.

With me ready to go I bent Paulina over the edge of my bed while lubricating her a-hole with my gloved hand. Wiping my hand off holding her by the hips I began to slowly insert the strap-on while she attempted to tense up. I let her know strap-on training was necessary for all sissymaids and that I had allowed her to see and touch it in an attempt to get her used to it. Now I was going to train her to accept my strap-on so stop tensing up and allow the strap-on inside.

I reached down playing with her cage penis and balls as I inserted the strap-on. It went in easier with her thoughts preoccupied as I played with her balls. Paulina was beginning to moan as an slowly shoved more of the strap-on into her then pulled back to see if I could still hold it inside me as well. As I moved in and out of Paulina the strap-on pressed against my clit which was starting to excite me.

Talking to Paulina as I began to fuck her telling her about her uncle loving the strap-on too. I asked her is she was doing alright with the usual answer yes Mistress Joanne deep breath from her as I began to pick up some speed causing her to move around trying to get comfortable. Helga the feeling of her pushing back on me was making me horny because her movements were making me hornier as the strap-on moved in my vagina.

Before long we were both moaning as I fucked her harder and she push back on me harder. This went on for a few minutes when I slowed down to give her a rest for a minute. Once again I asked her is she was okay with a gasping yes Mistress Joanne so I began to fuck her more and more until I came.

I pulled out of Paulina wiping her down then had her remove the strap-on from me. She set it aside with me pulling her to the floor where I began to ride her face with my already wet vagina. Paulina brought me to orgasm when I rolled off of her onto my back. I called her to suck on my breasts as a reward for having her ass fucked hard.

Within a few minutes Paulina got me ready to go again so I pushed her face back into my waiting wet vagina. It didn't take long before I orgasmed again. Before allowing Paulina to get up I instructed her that she was only allowed to wipe my vagina and never her face from now on. I explained that she should only wash her face in the morning during her shower. Paulina replied yes Mistress Joanne as I pushed her away from me.

Between you and me Helga that was the best night in a very long time. That strapless strap-on is amazing so I plan on using it often now that I tried it.

This morning while Paulina was getting me dressed for work I didn't talk about her ass or my strap-on. There are times we talk about things and times I want her to learn to deal with it on her own. The strap-on is a training tool so nothing other than bend over needs to be said.

Paulina was tender at least by her walk this morning yet she didn't say a word about it nor did she give me any attitude. When I say attitude I mean not be herself. It appeared as though nothing happened which makes me happy instead of hearing whining. Please let me know if you detect anything should she e-mail you today.

I'm off to work now.

Thank you for your letter Joanne. What a wonderful introduction to that amazing dildo, thank you so much for sharing that with me, as you might have expected.

You know, for me, her acceptance of becoming your sissymaid is amazing, I would have expected some push back of some kind, this seems almost too easy, what do you think? To push a man into this, to have him fight back some and to win that fight as he cries and pulls on his first pair of panties, there is something satisfying about that and in Paulina none of that was required, what a time saver, no problems or hassles, just immediate submission. How do you feel about that? Perhaps when the punishment starts, we'll see how she responds. In any case, I am so happy for you to be able to have a sissymaid back in your life.


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