The vacation, the real story

Well first off, before anyone gets too excited, the vacation was nothing like the fantasy I wrote before. That is not a bad thing though, for me at least. For anyone reading, I'm sorry if it is not as exciting as you may like. We spent for nights on vacation, but only played once. The first night we stayed in a hotel along the way. Mistress had me strip and get on my knees. She inserted a plug in my ass and clamps on my nipples. Stuffed my mouth with panties and a blindfold, and gave me a good spanking. After she was done, she had me put on panties and a bra, a pair of her jeans and go fetch her ice from the Ice machine. I still had the plug in and it was a pretty good walk down to the ice. No one was around, so it was pretty uneventful. The next day when we got to the cabin, Mistress allowed me to make love to her, wearing a condom of coarse, so as not to leave a mess. After I came, which only took about two minutes, she had me drink the contents of the condom. The rest of the weekend we were either to tired or simply too busy to play. It was very hard to stay submissive or feminine after this vacation, but Mistress had already set up a date, or better a sexual incounter for me later this week. I am trying hard to get back into the right frame of mind after a very un submissive weekend, but it is challenging. Don't get me wrong, I love my wife, and love times like we had this weekend, but it makes being out of control so much harder. Well more to follow on that, but I have to get busy getting pretty. Here is the outfit I think I will wear for my date.
What do you think?

The Relationship Changing Week

This week has been a serious struggle for me. So many things have changed and Mistress has discovered new powers and desires that to be honest I only fantasized about. She has become a hardened Mistress while also becoming more loving and affectionate at the same time. She has decided that cuckolding seems like a good idea. She has recognized the need for thorough punishments and that they must be administered at a much higher level than she had previously done. We are going on our vacation in a couple days and I have no idea what to expect, but she has promised more changes. Is anyone else’s head spinning yet?

So after all this news came about, tonight I am sitting here pondering all of this in a black bra and panty set, while Mistress is out at a bar with a potential Bull. I have been instructed to write about my feelings tonight and of the new changes. It is really too soon to know how I feel, it is all so new and unexpected. I know she is going to be disappointed, but for now all I know is that I am happy for her. She is starting to enjoy her role, and thus it makes me happy. I have flopped back in forth between happy for myself and sorry for myself, asking myself what I started. She has given me plenty of chances to back out; however she has informed me that I can’t be a man in bed the way she wants, so trying to be “normal” would never work. I am submissive by nature, and I will just have to learn my place and hope that this only brings us closer.  It is a struggle now, but I am sure I will quickly learn to love our new relationship. If not, I am also sure she will help me understand.

The rest of friday night

After my last post I got undressed, slipped into a pink nighty, and went to sleep. About two in the morning Mistress got home, slipped on her huge strap on, and with out even waking me up starting shoving it in me. She was tired so she only brought me to one orgasm, but it was still nice. We didn't talk after that, she rolled over and said she was tired. The next day she told me she had spent all night flirting with some guy and she had seriously considered bringing him home to fuck her in front of me in my full sissy state. Very hot and very scary thought all at the same time.

Friday night adventure

Mistress is out for the evening with a friend so I was given some instructions to do tonight. I got fully dressed, a pair of right jeans, a flannel shirt and high heel boots. After I got the make up and wig on, I walked out into the world for the first time. The task was simple enough, go to the local walmart, walk around and take a picture for me. Well it was so very erotic. I am dribbling pre cum still and it was almost an your ago that I left. Well I have to run, the second part of my instruction was to be in bed with a pink nightie on when she got home. More to follow on that later.

Early Orgasm

Mistress was kind enough to allow me to cum much earlier than I expected this time. I lated 18 days, but was expecting a month. I was relieved to cum early as I was falling into a bit of boredom. I try to hold of on my feelings when things are slow, but being new to this, and probably poorly trained at this point it is challenging. This was the first time that it was a single orgasm and back into chastity, which makes it almost feel like I wa never out. Last night, Mistress came home from work and immediately got into her strap on for some play. It want anything fancy, but she quickly gave me four good female type orgasms to put me back into my place. After lounging around and having dinner we went of to bed and Mistress had new fuck her with the strap on. She did not get enjoyment out of it and went to sleep very angry with me. we will have to see what punishments tonight bring.

Todays Story

To start this out, this won’t follow my traditional line of fantasy stories, or stories that I hope to actually happen, but rather just a quick entry to how my day has went. I will probably be drifting in more of this direction in the future, as the long stories usually require a lot more time than I generally have. I have also had trouble getting followers and comments so maybe this will help things pick up.

            I woke up this morning early, in a normal day off gurly mood. I painted my toenails, shaved from head to toe, and then headed to the gym to workout and spend some time working on my tan. I always enjoy my time in the gym, even though now I spend more time getting a femme figure than lifting weights. I always wonder what others think when all I do is leg and ab exercises. Then its off to the tanning bed where I wear nothing but my cage and bikini bottoms. Today was especially fun since I had pretty pink nails to stare at the whole time. When I left the gym, I got a text from Mistress telling me to fuck myself with the large, and I do mean large, dildo at some point today. This thing is huge, its 2 ½ inch in diameter. Mistress intends on this being the dildo she uses on me in the future and wants me to get used to it. She also told me to send her pics so there was no way out of it. Surprisingly it fit well today and once the pictures were taken and sent off, I achieved two really good female style orgasms. I miss cumming like a man, but have to say female ones aren’t bad at all. She told me that tonight, my clit will be coming out of the cage for some serious teasing, and somebody was getting fucked hard tonight. Not sure which one is wearing the  strap-on, but one thing for sure, it wont be my pathetic clit.

Vacation Part 2

For the sake of the story, we will say that I was unable to achieve the ruined orgasm in the time allowed and was put back in the cage. Mistress ordered me to dress and handed me her large dildo and told me to bring her to the usual two orgasms. Once I had finished making her scream in pleasure, she ordered me to clean her up. “how does it feel to have your mouth in a well used, stretched pussy.” I just nodded and continued licking her pussy which was more stretched than I had ever seen after the two days of large cock. Once complete cleaning her up, she got dressed and we headed out for the day. When we were out she asked me why I thought she had chosen the large cock all week. I told her I wasn’t sure, and she informed me that it was because she truly did like being fucked by a real big cock now and even though I was ok sized, she needed much more. She also added that if I was lucky enough to get in her this week, it wouldn’t do anything for her so she would not feel as if she missed my pathetic cock the next go around. That night, I fucked her again, same as always, big cock, two orgasms, clean her up afterwards, all the while being degraded.

            The next morning she offered me the same deal as the day before. This time however, I succeeded in milking myself on her belly and with only a little hesitation cleaned up my mess. She left the cage off and had me fuck her again with the large dildo, same as before. I was really frustrated this time since I was free, but still couldn’t enter her. I cleaned her up and we spent our day on the town. I was really hoping that when we got home I would get to finally enter my Mistresses wonderful pussy. When we entered however she handed me the dildo and smiled. I knew what I was suppose to do. As she took off her pants and panties, I inserted the plastic cock into my fly and slipped on the condom. Mistress had me sit on the couch and she lowered herself on the giant dildo. She had chosen to ride it this time. Very slowly grinding it she brought herself to orgasm several times. She settled fully down on the dildo and looked me in the eyes. “Does your little cock want to cum in me?” I nodded my head and told her yes very much so. “Fine, but here is the deal, you can fuck me as many times as you like tonight, cleaning me out each time and you will be locked back up tomorrow for another four weeks. Or, you can wait another chastity period and have sex with me the remainder of the month.” So basically I had to gamble here, one night of orgasms now for the month. Or, take the chance that my next period would only be ten days and get two weeks of sex. If I got in trouble or failed in any way a week of that would be gone. I have never had such a hard choice in my life. I had just done four weeks, and knew how hard it had been, but I also knew that taking the chance was foolish since she had made me fail on purpose last month. The longer I sat there and thought, the longer that huge cock was inside her. She was in no hurry for me to decide, as I could tell she was about to cum again.

Maybe the readers of this can help me out?