
Later on when we were "ready for bed", I surprised her with the strap on. I think she knew it was coming but I made her think it would be my larger than life size, but I was nice and used the one about the size of her sissy clit. I could tell she enjoyed it quite a bit because she moaned a few times. I did not have her gagged this time because I wanted some feedback on the strap on. It has been a while since our last session so I wanted to know what I was doing right and wrong. She liked it, a lot, hahaha, I know she wanted more because it's an unfamiliar type of pleasure... it's painful yet enduring. I think I had hit the nail on the head too because she kept begging me to cum, but I just told her "NO!". I love being in charge.
Monday was uneventful, she cleaned and did her usual chores. That night I let her play with me, it got pretty intense. My vibrator has many speeds and she kept going back and fourth through all of them! It was amazing and intense. She's not the best with vibrators, fore play or any sexual things other than vanilla sex. Although I must say, her vanilla sex is always awesome! That won't be happening for a long time though :). I actually had to have her stop pleasuring me because it was literally too much for my body to handle I can't remember exactly but I think I had around 10 orgasms. It was the best job she's ever done. I was very proud of her. When we finished we laid down [she still gets to sleep in the bed beside me for now] but to keep her in her sissy place I made her keep her face in my ass until I fall asleep. It is quite comfortable, I love the heat from her breathe in between my legs, it gets me all wet. Tuesday and Wednesday were about the same as Monday since I am trying to get all my training and such in order. Plus we had to work on some stuff for the house that couldn't be put off anymore because we're having painters over on Saturday. [ Ugh Housework!] It is so nice to have a home of our own though, it is definitely worth all the hard work.
Thursday, probably one of my favorite days yet! I had arrangements with a friend to go to this art thing for her birthday so we got to paint and drink champagne it was fun and entertaining. When I got home Debbie was not in her attire like I had told her to be which got me a bit weary whether she ever had her chore clothes on. When I approached her and I asked her why she was in normal clothes; I realized she had a good point, she did not want to get the clothes dirty because I had worked so hard on making them for her. She was doing messy work on the walls and it was all over her. So I still told her she should have asked first, but it was "okay for this time only!'' [mostly because she had attempted to call/text me but I did not check my phone]. Well, we finished up the painting prep work so I told her to get ready for me to train her. I had been planning for this all day and was really looking forward to it. I helped her get dressed and she looked so damn cute in her new outfit I had made for her! I want to make at least 3 more petticoats so it is EXTRA BIG and POOFY! I had heels on a told her she needed to start observing how I walk in heels. I told her she had to shake her sissy ass more than I do when we get her some heels.
After we walked around for a bit and I showed her how to walk in heels, I had her practice "greeting me". I mean when I get home from work I want her to greet me a specific way. Every single time. If she does not do this I will put her in her cage and put the files I've been making her listen to on for an hour. So when I arrive home from work, she is to be on her knees and wait until I come in. I will put my hands out for her to kiss both, if I want her to kiss my ass or feet she will proceed after. Then she is instructed to ask how my day went. She will then take my stuff and put it away. I'm going to be on her little slutty ass if she does not do this greet right in order. I will give her one try tomorrow and she better get it right or into the cage she goes. After the greet training I made her crawl for a long time. She has wrist locks on with about a 3 foot chain holding her ankles together. To make it more difficult I pulled up on the chain and held it so her feet wouldn't be touching the floor. Just another "obstacle" for her. It was difficult and I'm sure it hurt her knees on the hardwoods. We have hardwoods in almost every room so I may have to get her some knees pads. HEHE. I Should put some girly frill stuff on them too! After a while of crawling it was to the bedroom.
I let her listen to the files while I got her "ready" for the strap on. I first used the vibrating dildo, then I plugged her for a few minutes again to get her ready and then I used the strap on. She really thought I had the big one again! :) I am going to be nice for a few sessions until her little slut hole gets more used to it. It was awesome. I never would have imagined I could get off to the feeling of fucking a guy. So that was an amazing end to our wonderful day. It was a good step towards feeling better about this lifestyle.
To say the least, I am very excited about what comes next. I cannot wait to see where this journey leads.