Anonymous Sissy

[Reposted from my old site. Original from May 11, 2013]

For a long time, I toyed with the idea of visiting a dominatrix but I never really felt comfortable taking the leap. Then, after another day of looking at websites, I found Ms. Lori’s and I was hooked. I sent Ms. Lori an email describing the kind of session I was interested in (cross-dressing, bondage, impact play and foot/strap-on worship) and soon had a very enthusiastic reply. Any reservations I still may have had were completely gone, especially when I saw Ms. Lori’s detailed questionnaire. I felt so comfortable at that point that I already couldn’t wait for our first session.

We agreed that for our first session, we would do some shopping to pick out an outfit for me to wear and then spend a little time transforming me and playing together. I met Ms. Lori outside the store she chose. As soon as I saw her, all nervousness was gone. She is absolutely beautiful and hot – her pictures do not lie!!! Before we started shopping, she wanted to make sure I was ok talking about finding the clothes for me and trying everything on. I was still a little embarrassed to be shopping for women’s clothing but Ms. Lori made it fun and exciting. We purchased a dress and then headed to our next stop for the remaining items. From there, it was to the dungeon for our first session. Ms. Lori did an amazing job making me look like a woman (the women at the dungeon even commented as to how well she made me look). Once dressed up, Ms. Lori gave me an amazing spanking – not too hard but not too gentle. It felt amazing. And her strap-on… I was quickly her sissy slut and could not have been happier.

I had such a great time, I could hardly wait for more time together. For our next session, we had some shopping to finish up and then we went to the dungeon to make me a woman. Once again, Ms. Lori did an amazing job. From there, it was out for a couple of drinks together. I was a little nervous about going out dressed as a woman but with Ms. Lori at my side, I felt like I could do anything (it helps having a beautiful woman at your side while dressed up). As soon as we left the dungeon we were hit on. We walked a few blocks (my first time in heels) and then stopped at a restaurant for a few drinks. Ms. Lori was great – she made me order my own drink and talk and act like a woman, and she treated me like one too. Then it was back to the dungeon for a little more play time.

Even better than our first session, Ms. Lori tied me up, pulled my panties to my ankles and then said we were going to play a little game – I had to count each stroke on my butt but I had to keep track of each cheek. If I miscounted, we had to start back at 0. She collared me and put the leash on a hook to keep me from squirming. I was so excited it took a little time for me to get the hang of the game with everything else going on but I did soon enough. I was then walked over and tied to a bed to lick Ms. Lori’s feet and, once again, prove that I was her sissy bitch. Ms. Lori was amazing – she covered my eyes at times and the anticipation of what was coming next was so unbearable – I loved it!

I can’t wait to see what she has in store for our next session!!