Let me just back track a few days, Sunday we had a GREAT day! It seemed that everything went so smoothly. I let her go do her hobby in the early morning since I had plans and then when she arrived home we went straight into full action! I had her get dressed head to toe in her maid costume (a different one that the last post) and she cleaned up all the dirty clothes and tidied up the house very nicely. After that we did a nice few hours of isolation time [which I think will become to norm of our sundays]. The isolation time is complete with earphones that keep out most noise, blindfold so no light gets in her eyes, a nice medium size butt plug and each of her limbs securely chained to all four posts of the bed. hehe :) I usually just keep her in a full diaper during the sessions that way her diaper is super heavy and full by the time they are over. She seems to make a mess more when the files play.
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.
Hi Madam. Reading about your relationship saga with your sissy, I have to wonder, was there a turning point or specific moment where you realized this is what you wanted? Was it the authority over Deb's orgasms and the control that can come with this-being more than just a game? Just wondering, since you really seem to have embraced it after having some initial doubts. Have fun,
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Fran's, yes there was a turning point. When I failed the first two times it was because I did not research or read about any others in this lifestyle. I spent a lot of time the past few weeks reading and thinking about if this is what I wanted. Everytime I came to that question all I could think was " yes!" With excitement. I did not think I would be so natural at it but I guess I kind of am. I feel more alive when I'm in control. I don't normally like controlling or making decisions but to be in complete control when she gets off ( or dosen't) is pretty invigorating. I'm loving every moment and cannot wait to see where this goes, I think it was the look in her eyes when she was literally begging for an orgasm. I just said nope! It felt so good!
ReplyDeleteFound your blog today as well as "Debbies". Very exciting and informative. Thank you for sharing. Have you considered training her to cum on command as you peg her? Also do you plan to have her suffer/enjoy some stealth public feminization as in panties/stockings at work or hair styling/ body shaving?
ReplyDeleteAnd one final request would be that you might consider to post some actual photos with faces/details obscured...think of the humiliation possibilities! In any event yourblog is terrific. Keep going!
Love your blog! Have you thought any about public diaper humiliation? Or making her wear a thick diaper under her clothes so she waddles when shopping? Will Debbie ever be diapered around your friends?
ReplyDeleteFirst, I have thought ab training her to Cum on command, I have a little frustration when I drained her the other day, I have her a ruined, I will talk ab that in my post tomorrow :) . The ruined are very frustrating and I could tell I did it just right bc the look on her face was pretty sad. Feminizing, I've already started that I used gel cream hair remover "veet" to get rid of the hair, it worked great! The only problem is we let it set too long and it says not to let that happen but we miss timed it :/ it turned out pretty smooth but it could have been better if we did sections rather than trying to hurry and do everything at once. I Have considered the possibility of making her wear some feminine thing, diaper also but it just depends. I have definitely thought about real pics :) I will do that in time. With all her hair shaved you would never be able to tell who it was anyways since I'd have to block out the face, she works for a pretty prominent place ;). Diapers in public, it cracks me up I would like to do it, but it couldn't be in our hometown, maybe on vacation!!!?? (Pondering that now!) yes Debbie will more than likely be diapered around some of my most trusted friends! Girls gotta have a good laugh every now and then! I wound also probably make him serve us wine, cheese or some kind if fancy food on a silver platter in his diaper!!
ReplyDeleteAll sissy's should be Cuckolds.
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Keep up the great blog!!!! People are wanting more!!!! BTW it's your "coach" check your inbox on the mansion, sent you some "inspiration"
ReplyDeleteAmy