Maid to serve (lifelong fantasy fulfilled) (week 1 chastity assignment)

I posted here awhile ago. I am happy to say that after a lifetime of shaming about my kinks I am finally in a relationship with an amazing woman that accepts and plays along with this part of me. She loves to dominate me and prefers I call her master.

We have played multiple submissive games over the past few months, but always ends the same: I beg her to let me out of chastity and she agrees and then for a few weeks after I pretend to be the dominant male having sex with her at will.

This time, however, I couldn't help the craving for submission coming back. My master sensed this and after these few weeks of faux dominance ordered me to lock my chastity cage back up for at least 2 weeks. I agreed, and promised to commit to her completely and not beg my way out of it, no matter how long she plans to deny me. We are currently in a long distance relationship so most of her domination occurs via snapchat and facetime.

She agreed to play a few games with me:
(1) when my release date comes, give me the option to orgasm in an unsatisfying way or offer a satisfying orgasm if I wait even longer (i.e. keep delaying release
(2) every week we agreed to come up with 3 "assignments" that she had to approve (2 from me and 1 from her) and I had to do all 3 in order to receive my weekly reward of a prostate milking

I had one of the most erotic and sexiest days of my life on Saturday and fulfilled a lifelong fantasy. Master assigned me to clean the entire house top to bottom while dressed to the nines as a french maid, complete with makeup and high heels. I got hard in my cage just thinking about it.

I thought I would be able to do this in private, but master wanted me to facetime her. I have never been before anyone else in women's clothes before, so I was really scared that this would be too much for her or for me, but I was too turned on not to try. She said that she was looking forward to seeing how bad my makeup was and how humiliating it would be for me.

The maid uniform I bought online in multiple pieces to make it perfect. I bought the sexiest maid outfit with garters, but it also had an air of practicality and authenticity. It included a little lace tiara and lace wristbands and a lace apron. I bought black lace ruffle panties that perfectly matched the outfit, and also white thigh high stockings with seams. Finally, I bought size size 15 black pumps with a 3” heel.

So I started getting ready. I put in my largest vibrating butt plug and got dressed in the entire outfit. I made sure the details were just so: the panties were under the garter straps and that the seams were straight, etc. Honestly, the most humiliating part of it were the lace wristbands and tiara. I stepped into my heels which fit pretty well but were a bit uncomfortable. My little cock stiffened in its chastity cage.

I didn't want to go nuts with the makeup since my skills were limited and I knew master would be expecting it. I put on some foundation, concealer, blush, powder, eyeshadow and mascara in a fairly conservative look. I put on light pink lipstick and messed my hair up under the tiara.

I was terrified, but I facetimed Master. I started pointing the camera at the ceiling, but after a few minutes I showed her. She was actually impressed by my makeup, she said it was “not the worst,” and she was “kind of angry that it wasn't worse,” I think she wanted to make fun of me haha.

I also told Master about the butt plug. I always assume that Master wants me to wear a butt plug to know my place. This time she said no, that she didn't offer me that pleasure this time. She said for doing that without permission, my punishment was that I lost my milking privilege for the night (she knows I need a dildo not a butt plug to milk myself). She said the butt plug would have to be enough stimulation. I begged her to please reconsider but she said no.

I showed her my makeup, the heels, I lifted the hem of my dress and showed her the panties and stockings. I even showed her the lace wristbands. I was so utterly humiliated. She told me to open the blinds and let the neighborhood see me work but I was too scared. So instead she told me to put on the spiked cage while I worked. I asked her please no, and she said very dominantly “are you telling me no?” I realized that she would add to my chastity time if I didn't do as I was told. So I went and put on the spike cage.

I asked her what she would do with me if I was there physically (we are long distance). She said “nothing except spank you.” It was SOOOO FUCKING SEXY to be in front of her that way.

The outfit felt so good physically. I felt the breeze on my bare thighs and shoulders. I had to sit on a chair and I felt the cold chair on my bare legs under the dress was the first time I had ever felt it and it was exhilarating. The stocking and panties and dress hem was tickling and teasing me the entire time.

I used the feather duster to dust the baseboards and surfaces, and then used the mop to mop every floor (the apartment is all hardwood and the bathroom is tile). I then got down on my knees and scrubbed the tub and sink. I asked master to call me a maid slut or a sissy maid, but she said no that I can't ask for that kind of thing, I am just a sub. Put me in my place.

My feet and calves ached from the heels. I couldn't believe how unsteady I felt when I stepped OUT of the heels. It felt like when I stepped from heels to the ground that the heel was the “normal height” and now I was unsteady. Crazy.

I called Master to tell her my chores were done and asked her once again if I could have my milking after all, even though I was bad before. She gave me permission, and I thanked her like crazy.

I stayed in the maid outfit the entire time. I was worried I would get it dirty at first but it was such a fantasy to be the slutty maid being penetrated in her outfit. I was at it for over an hour and had at least 5-6 little spurts. I tried really hard to have a prostate orgasm but was unsuccessful (as usual). That's usually how my milkings go. Lots of stimulation, then a little contraction in my little cage with a little rope of cum shooting out. It's sexy to watch for me. It does feel good and does “take the edge off” physically, but it is psychologically frustrating and submissive-feeling because I am slightly physically satisfied but not psychologically satisfied. So it reminds me that I am not in the male role and did not get male pleasure. The frustration and denial is so fucking sexy.

Like any good milking it feels good even now the next day. But moreso in a way that makes me horny than satisfied. I told Master how horny I was and she said “at least you got to cum.” I love it when she shoots me down. She said I have at least a month to go so let's see where this goes!

 

Thank you for all the feedback! Im very happy you all enjoyed the writeup.

Although i havent posted I have been reading your responses. Master made me read my original post to her out loud as well as your responses, which was also humiliating.

We are still in the midst of a chastity session. Tuesday will mark 6 weeks! A new record for me to be sure. She has been gracious enough to grant me regular milkings. She has really taken to this dominance thing, but in her own way. She has only assigned me things that she likes and i dont (painful punishments\toys, waking me up out of dead sleep to stroke to an edge or do aerobic exercise for her, etc).

Most tantalizing of all she has made me ask for every single little thing that provides any pleasure whatsoever. If i want to wear panties to work? Have to ask. Do i want to put on makeup and use a dildo? Have to ask. Put on my maid outfit and clean thr house? Have to ask. Asking for these little pleasures is so humiliating and makes me admit what are my pleasures versus hers, and what a”pig” i am in her words.

Of note she is visiting me sunday after 7 weeks of long distance. She has already said she isnt going to unlock me and made me promise to not listen to her if she offers to unlock me during the throes of passion. Ive had a really hard time maintaining chastity in her presence in the past. She is so sexy that i just need her so badly. Ive spent the time channeling that energy into reading about new oral sex techniques to try on her, and i intend to try to stay locked. I will use a strapon on her and i asked her to return the favor to me. I can only hope im that lucky.

She is also talking about tattoing me with her name or “sub” on my skin. Cant wait for her visit!

 

Hey girls, wanted to post an update.

A few weeks back I got a visit from my master and we had a great time. I was 1 day shy of 6 weeks in chastity when she arrived, I was ready to burst. I gave her a whole body massage and got a chance to showcase my new oral skills on her and survived an agonizing tease and denial session where she let me inside her for 5 thrusts but I only managed 3 before I had to stop before I had an accident. She locked me back up.

Later that night we did the same thing all over again, only this time I had an accident while we were fooling around. She yelled at me and said she planned to give me that reward on my 6 week anniversary but I failed to make it there. She had me get her creampie off orally after that which is a major fantasy of mine as well, but very difficult when I lose interest after the big O. I still did my job.

Our sex life was pretty "normal" for the rest of that weekend. After she lets me finish and the long chastity is over, she often won't lock me right back up so that we can enjoy each other for awhile, which was great. I needed the break honestly I had started to crack during the 6 weeks.

The last night of her visit I asked her for a BJ. She asked me if I wanted to try pegging like I had been begging her for for the 6 weeks. I said yes. She said I would have to give up the BJ to experience that pleasure. I agreed. I think she liked making me admit that I wanted her to do me more than I wanted to do her mouth. It was a bit like having sex for the first time again, trying to find the right angles or positions and we didn't get it just right, but she did a great job. She let me stroke while she was doing it. I was so horny.

She kept going until she was exhausted. I begged her for the BJ and she said no that I decided against it remember. I asked if I could finish in any way she said to suggest something: I suggested to finish on her chest and lick it up and she agreed. I finished and before I could even think she commanded me to do it and made sure I didn't miss a drop. There was so much of it...

Afterwards she complained that the 6 inch she used was way too small. I showed her the 8 inch I had bought as well as part of the set. She said still too small, she said that's an "average wiener" (god knows what she thinks of my size then ). She said if she's going to do it again she wants it to be a challenge. She decided on this one

https://www.edenfantasys.com/dildos/rea ... d=74300439

It hasn't arrived yet but I am terrified of it. I asked her for a few more sessions to work up to it and she said she would think about it.

One other development during the weekend is that she began calling the maid (me) by a girl's name (Ericka), which was also super hot.

After she left she gave me one more day of freedom to masturbate (which I did fantasizing about her pegging me). When I asked her the next day if I could do it again she said no I had to lock it back up. I asked her not to and said I needed more of a break after last time and she said she wasn't asking and to go lock it up. So now for the first time I am in chastity 100% by her will, which was extremely hot. She has also sent me links to some dominatrix stuff she has been watching and reading- very sexy to watch this side of her emerge.

She gave me a chance at a milking at the one week mark if I took a jog around the neighborhood wearing only her leggings and a sports bra. She said if I got caught I would have to tell my neighbors I was doing the "sissygirl challenge." I got dressed up and looked so hot but ultimately chickened out and put a white tshirt over the bra. Everything was still pretty visible but Master wasn't happy and revoked my milking privileges.

I am seeing her again this weekend after nearly 2 weeks in the cage. To say I can't wait is an understatement. The last few months have been a ton of fun.

 

Oh believe me after a 13 year relationship where i had to hide any kinks i had, i know how lucky i am. Master sees the real me and loves what she sees and vice versa. Its amazing.

Thanks for responding! I do lurk on the page but I only post when I get permission from master. She always makes me read what I post out loud to her which is extra humiliating.

As I said in a previous post she’s been making me ask permission for anything pleasurable including posting for attention.

After my last post I did see her that weekend. We didn’t do much fantasy stuff that weekend. She let me out for the weekend and for about 2 weeks after where I got to cum pretty regularly (asking for permission each time obviously).

But last week she demanded that I be locked up again. I objected but she didn’t care. It’s hot that she’s enforcing this on me even when I don’t want it. I’m about a week into lockup this time. She’s been saying it’s going to be 12 weeks this time. I seriously almost died after 6 weeks last time so I’m hoping she takes mercy on me before then. She said the other day her final goal for me is going a year at a time with a single orgasm. It’s hot to think about but I’m terrified.

she has forced me to try the huge dildo on my own. She has had me stroke it for her, hold it up to my own parts and remark at the size difference, and eventually work on inserting it. I can take it inside and rock back and forth but can’t thrust it in and out. We haven’t tried pegging since the first time. I hope we try it again soon, but again I’m scared about her being so rough with it.

a few months back I asked her to dress as a maid and clean the house in full makeup. She said yes. She even called me by a girls name! Ericka.

One thing that wasn’t great about the experience was that I actually did a good job with the makeup heels and outfit but my hair was still boys hair. Destroyed the look.

So this week I asked master if I could add a wig to complete the look for Ericka and she said yes!

I did some research and settled on mxangels brand as the best mix of quality and price. I bought a stocking wig cap and this wig arrives tomorrow and I’m super excited!!!

https://www.amazon.com/Mxangel-Medium-C ... 67&sr=8-15

 

Sissy Ericka reporting in.

After a few months of "pretending" to be male, my Mistress decided she was tired of my wishy washy half maleness and my small package failing to satisfy her (she seems to love the small penis humiliation, perhaps even more than me). This time, she made me promise that I would be a good sub this time and from now on before she would let us start playing. Because I had been so bad lately she made me agree to at least a 3 month chastity sentence (she wanted to double our previous best of 6-7 weeks), with the possibility for longer. She was going to lock me up without a final cumming but I begged and begged and she mercifully agreed to give me a "sendoff."

As usual, she gave me the choice between a BJ and a pegging, with both of us knowing I would choose her strapon. Something about my turning down something "manly" in favor of something "sissy" reaffirms my role for both of us and gives us a thrill.

She made me suck on it before putting it in me, but said my technique was terrible. We have done peggings in the past, but it was always a bit awkward in terms of body position (in no small part because she still insists on using her 11 incher despite my pleas to buy a smaller one).

This time I decided I was going to go all in. Instead of asking her to pound me doggy I rode her reverse cowgirl, grabbing her hips for extra leverage. I found that perfect spot and kept at it. I had begged her to be more verbal in her humiliation of me so she kept saying she wasn't going to let me cum after all, so I would keep begging. She also said she was going to make me lick the cock clean when I was done, and finally called me a slut and told me I could cum as long as I caught it all on my pink plate and ate it. She made me eat the cum, but spared me cleaning the strapon.

After orgasm, I predictably tried to get out of wearing the cage. She reminded me of my promise to be a good sub or never play again. So I put it on and gave her the key on a necklace.

So I've been caged and in panties for nearly 2 weeks now. Mistress has had full body massages every night and had chores done for her. Haven't yet put the maid outfit on because "I take too long to play dressup when I should be working." I guess I have to earn that.

We went shopping on Sunday and bought some women's workout clothes for us to share. We now more and more are sharing a wardrobe since our bodies are mostly compatible for some things (she borrowed my sundress recently and got a compliment from a girl while wearing it- jealous of how much better she looks in it!), and she even gave me an eye makeup lesson on Halloween which I wore out to the bar! It's been great so far.

I haven't asked to cum because I know that would just add to my 3 months. I begged her the other day to immediately force me back into the cage the next time she lets me out, so that I don't weasel out. She said it's not an issue because she's never going to let me out again.

But she has verbally agreed to a teasing session and/or a pegging/milking in the "cumming" days, so I guess I have that to look forward to. During our previous record of 6 weeks I did some self milkings, but am looking forward to having a partner.