To officially become a cuck tonight?

Mistress is out at a concert tonight. She has been very dominant lately and things seem to be much more elaborate this time around. I don't know if she has plans yet, but she is a very attractive woman so I'm sure she can find a volunteer. I was a good sissy and sloped a couple condoms in her purse just in case. Many things have happened over the last couple weeks and I will do my best to share those stories with you all soon. But to keep this from being to long I will sum it up to say that I am now chaste till mid july, and have been exiled from Mistresses bedroom so I'm sure being chucked is the least of my concerns by three time july gets here.

Slowly returning to submission

For the part few weeks we had a break in or dominant submissive lifestyle. Mistress has just got a new job, where she will be on the road during the week and we won't see much of each other. We took the break to see just how we were going to cope with being a part and maintaining our lifestyle. We are pushing forward again, and taking it slow to make sure everything goes smoothly. I am sure it will and now that she is truly the bread winner, I may slip further into

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?

Vacation Part 1

So we off on our second honeymoon vacation. I have been locked away securely for over a month now, for various reasons I will explain shortly. This has been my longest straight chastity period. Mistress has assured me that she will unlock me as soon as we get there. I am so excited I could burst…and I mean literally. Mistress has spent a lot of extra time this past week making sure I was on the verge of insanity with need. I have spent hours being teased with her in sexy lingerie. All week she had me put the large plug in my pussy for an hour before bed. I was at an all time high in submission.

            So how did I end up in chastity for such a long time? It started shortly before Christmas, when a poor discussion got me locked up early. That night Mistress told me it would be three weeks in the cage, and for every time I failed to please her it would be an extra week. When she told me this I was sure I wouldn’t see an orgasm till early spring if I was lucky. Amazingly though I did very well and with only a few days left of the three weeks I was very proud of doing everything she had asked and managed to make her cum every time she told me to without her having to take matters in her own hands. I have to admit Mistress helped by not asking for a lot of orgasms but did make some truly humiliating demands, but as a good sub I did without question. With only hours left to my original period, Mistress tied me to a chair in the bedroom, blindfolded me, and teased my nipples. Soon she clipped the weights to my nipples and walked off. I thought that she was going to leave me like this for the night. Then she spoke in her cutest sweetest voice to me, “baby, can you come over her and please me?” I sat there in silence for a short while before I told her that I couldn’t. She laughed and said “guess I will do it myself then”. She quickly tossed herself off, cumming hard and loud. After she settled down, she came over and took the nipple clamps off.  She leaned in, kissed my cheek and whispered, “That’s another week”, and went off to bed.

            We talked and enjoyed our ride through the mountains. Once checked into the cabin, I was told to strip and get on my knees. Once there, Mistress spoke to me in a kind way, “I know you are looking forward to a long week of fucking me whenever you like, and you will, however there is one small problem. You will be doing it with a dildo.” Shocked I looked up at her in disbelief. “This is going to be the honeymoon that I wanted and you will be a good submissive and make me happy. You have two choices, either be a good sub and fuck me with the cock of my choice or have an attitude and I will fuck you with the dildo of my choice all weekend.” With that I nodded and handed me her largest dildo and told me to get dressed and bring her to two orgasms. I put the large cock in my fly and slowly pushed it into her stretching pussy. After she reached her two orgasms, she kissed me and said lets go to town. We enjoyed the night shopping and getting dinner. When we got home, she had me use the same dildo on her again to bring her to two more orgasms. Her pussy was getting accustomed to the large cock.

            The next morning Mistress had me get naked. “Here is the deal, I will unlock you today and you can stay out of your cage if you can follow these instructions. You get five minutes to achieve a ruined orgasm on my stomach, and then you will clean it all up with your mouth. No pleasure allowed no spurting, grunting or having a full orgasm. If you fail any part of this you will be locked back up and we will try again tomorrow. If you succeed you can stay unlocked today and maybe you can have an orgasm tomorrow.” After acknowledging her she unlocked my cage and I started stroking.

To be Cont……         

Birthday story prelude

A week before my birthday Mistress asked me what I wanted to do for my birthday, so I started thinking, unsure of my commitment at this time. Last year at my birthday dinner she made it very clear we would always have some kind of dominant submissive relationship. This year, I have already been in chastity for over two weeks, and no idea when its going to end. We have already discussed a system that requires me to be submissive and chaste for a minimum of ten days a month. After that the remaining 18 days are up to her discretion. So I have sit and pondered, and have come up with my thoughts of a nice submissive birthday and birthday wish.

My birthday is on a friday night this year, so that makes things a little easier. Mistress sent me an email early in the morning.

Happy birthday slut, when you get off, go straight home, and get yourself ready for me. I want you to be naked, the small plug in your pussy, blind folded, and tied spread eagle to the bed. Tie you feet and one hand and I will get the last one. I hope I am not late, but you know how fridays can be.

I don't know how long I laid there, but I had fallen asleep, I'm guessing a couple hours by the time I saw a clock it was after eight. When Mistress came in she lightly stroked my clitty til it was hard. Then she got of the bed and I heard the bath running. She came back in the room and placed clothes pins on my nipples, and went about getting her bath and getting dressed. Soon she was sitting on my face with my lips touching her rose bud. ” don't move until you can't hold your edge anymore, then I want your tongue deep in me.” I could feel her hot pussy on my chin. Once again she slowly stroked my clitty, but this time pushed it to the edge.  I slipped my tongue in her ass to let her know I was close, but she didn't stop. I frantically stuffed my tongue as deep as I could and she released my clitty. I tongued her deep for a few minutes before I felt her rolling a condom down my shaft. ”Keep this on tonight, I want you to have desert” she chuckled. She got up, removed the clamps and butt plug, finished dressing and untied me. I got dressed and headed to dinner.
When we get to dinner she tells me to answer one question, depending on the outcome, it will decide a few things about the night. It may be guessing if she wearing panties or not, or some other question. Something she had thought up to suit the odds she desires. But, before I guess she will tell me the results of guessing right or wrong. ”Either way we are going to go park somewhere. If you guess correctly, you will be allowed to eat my pussy in the car before we go home, if you you are wrong, you are going to suck my cock and then I'm going to fuck your pussy in the car. After we return home there will be more choices for you to make and more surprises.” She told me that She had a present and two cards on the table and told me that I only got to pick one card. One card read that I got my wish, and the other one was her wish. Both cards were simple envelopes, with no way to tell.  I will follow this story with two different  endings.  I didn't know which I even wanted, I didn't know what her idea was and it could of been worse than mine.
To be continued.....

Tease Session

It has been nine days since my last orgasm and I am finally getting in the groove of submission again. It has been a struggle but I feel myself slowly turning. Last week, Mistress decided that I needed to spend some time out of room so maybe it will set in faster. I am also under instruction that while I am sleeping in the other room, I am to write my fantasies on my blog every night so I will still go to bed horny. I am locked in my CB-6000 and not allowed to see her naked.

           

When I get home from work, we usually concentrate on the vanilla things in life since we have been talking about sex all day and I am plenty frustrated to get through till bedtime. Today however was a little different. When I walked in Mistress was in a sexy night gown and boots. I was about to tell how sexy she looked and as I opened my mouth she shut me down.

“Go to my room, get naked, get on your hands and knees and keep your eyes down and mouth shut” Mistress demanded.

“Yes mistress”

I did as I was told and within minutes was waiting patiently in her room. When she came in she led me over to the end of the bed, placed a blindfold on me and took a seat on the cedar chest in front of me.

“I wanted to get some playtime in early today, before you spend the rest of the evening in your room writing your stories” she said as she laughed a very new and cruel sounding laugh.

She stood up and walked behind me; I felt her applying a small amount of lube to my ass and gently massage it. The next thing I felt was a glass dildo sliding up and down the crack of my ass, then slowly pressing against my hole. After a good five minutes of teasing she slowly inserted it several inches into me. Reaching down under my chest she began to massage my nipples. It felt incredible in combination with the dildo in my ass. She then proceeded to take the heavy two once nipple clips and handed them to me to apply to my nipples.

“See if you can’t keep that dildo and those clips on till I am finished with you. If any of them drop to the floor, you will be punished.”

“Yes Mistress” I replied.

With that she took her seat back in front of me. She sat so close I could smell her sex and wanted to dive into it. I knew better than to do that without her permission. I heard her begin to play with her pussy.

“Why don’t you worship my feet while I masturbate and tell you a little story slut”

“Yes Mistress”

I began licking her feet, slowly and sensually as I heard her lubing up her dildo. Then listening to the sounds as it went in and out of her bare pussy only inches from my head. She then began to tell me the details of the conversation she had with her best friend at lunch earlier. She also told me that what I had been discussed in the past was merely a beginning and she would tell her or anyone else anything she wanted and to expect much more humiliation. As Mistress finished her conversation with me I could tell she was getting close and I could smell the juices getting stronger. Soon Mistress was moaning in intense orgasm above me and my poor clit was leaking profusely.

When Mistress recovered, she had me sit up and press down on the dildo. As soon as I got situated, Mistress took the soaking wet dildo and began rubbing it and her juices all over my face. When it began to dry she wiped it on her wet pussy and gathered more to smear on my face.  Once I was coated in her sticky cum, she got up and I heard her changing. Before she walked out she gave me my instruction.

“You may take the dildo out, the clips off, and blindfold off. Do not wash off you face because you are a sissy slut, and you deserve to be covered in cum. Once you clean up your dildo, I want you to take it and some lube to your room. You may spend the rest of the night writing.

The Car Wash

Early on Saturday morning I was woken before the sun came up . Mistress told me to go shave, she wanted to have some fun with Sookie today. I did as was told and took a bath and shaved. when I came out of the bathroom, she had set out a wardrobe for me. It was a pair of daisy duke shorts, a pink t-shirt and black high heel sandles. A black bra and black panties. I dressed up in the slutty attire, did my make-up and put on my wig. Once dressed, Mistress gave me her instructions. "My normal guy wasn't able to wash and clean my car this week, so you are going to go do it. I want it washed vacuumed and cleaned out. Take your time but make sure it is done right." i slipped out of the house and jumped in the car and was off. Unfortunately a good car wash was about a 30 minute drive away, so I was in for a good showing off. The leather seats were sticking to my newly shaved legs and making me very aware that the shorts I had on didn't cover much of anything. When i got to the car wash it was just beginning to get light, so i hurried along and washed it, got it dried, and began vacuuming before anyone else showed up at the car wash. Sure there had been a few cars drive past, but i kept my head down and my best assets showing. A man about my age had pulled in and was washing his truck as continued vacuuming the carpets, showing him my rear side as much as possible so as not to be discovered. I had felt the cool breeze on my long bare legs all morning, but now all i could feel was his gaze. He stayed and watched me finish long after he was done. I was very nervous that he was going to hit on me, but luckily he did not. I finished up, got back in the car and began my drive home. It was much lighter and i knew that the other drivers could see me clearly now. I was on an sexual high by the time i got home, and Mistress was more than willing to show me what the guy at the car wash was thinking about doing. She slipped into her strap-on, and slowly entered me. Once the head was in, she asked me if i wanted it and i said god yes. " Well then sissy, tell me about your day you little slut. Then maybe i will help you out. Mistress stayed right where she was, with the the head just inside me as i told her how everything went and answered her questions. Once she was satisfied, she fucked me to a half a dozen incredible orgasms, before we both curled up and fell back asleep.

Dream of Humiliation

Here is a fantasy that I had in a dream last night.


It was a Thursday night and i had the next few days off. I returned home, made Mistresses bath and was waiting for her to return from work. She sent me a text message telling me to get showered and shaved before she got home. I quickly did as I was told and just as i was finishing shaving she walked in. "Hello sissy girl, go ahead and tuck that clitty away before i get undressed" Mistress said. I did as i was told and tucked my clitty back and slipped into a tight pair of panties. She then went on to tell me "find a nice tight fitting pair of jeans, some heels, bra, breast forms, a girly t-shirt and the pink hoody for your attire tonight". She got in the tub and I went about getting dressed. I came back into the bathroom to put my make-up on. "It is very important you do a good job of getting pretty tonight, because i have a special treat for you. First off you are going out dressed, just as you are and filling my car with gas. Once you are all ready i will tell you the rest." I did my makeup and Mistress helped with the eyeshadow, put on and combed my wig and was looking my best. My heart was racing since i had never left the house dressed before. I had only had one other encounter with a stranger dressed, but thats a story for later. Once I was fully dressed and ready for what was to date the biggest adventure yet, Mistress handed me a purse and told me the rest of the plan. "After you get my gas, I want you to drive to a moderately busy parking lot. Take the dildo out of your purse and sit it on the seat next to you. get up on your hands and knees and give that cock a 20 minute blowjob. Just concentrate on the cock, and dont stop till the time is up. While you are away I am going to get set up for even more fun. when you get back, wait in your room until I come out and get you." It was already late and dark out, so I quickly ran out to the car and jumped in. I headed on my way to do my bidding. When I returned home it was nearly 10 pm, I sat on the bed and soon heard noises coming from the bedroom. Mistress was moaning and about to cum. She was also talking and yelling harder. After a few minutes she was screaming in orgasm. I laid on the bed wondering what my Mistress was up to in there. I really wanted to know, but knew better than to disobey. Everything was quiet in the bedroom now, and eventually I to fell asleep  fully dressed, wig and breast forms still in place. When I woke up it was morning, and Mistress came out to get her morning coffee. She asked me "did you have a good time last night? I know I did. You can change in here now, you have a lot of work to do outside the house today." I got changed and went about my day wondering what all had happened the night before, broken and terribly more horny then ever before. So did Mistress really cuckhold me or did she just put on one hell of a tease?