A Recurring Fantasy

I am currently beginning my third month in chastity for the pleasure of Ms Lee. My record is over three months so it is quite possible that my chastity will continue for a considerable time yet. I have never mentioned this to Ms Lee, but when I reach these extended times in chastity I begin to dwell on a recurring fantasy that I believe is related to the frustration I am experiencing due to knowing that Ms Lee could very well keep me in chastity for a lengthy and unknown period of time.

This fantasy found its origins in my curiosity about just how long Ms Lee might eventually expect me to remain in chastity for her. When we first began experimenting with me being in chastity the periods were rather short, just a few weeks or so. Over time the length of my chastity periods grew steadily, eventually exceeding an entire month. At that point I has thought she had achieved her objective and would be satisfied with me enduring an entire lunar cycle (or a woman’s cycle?) before I was allowed to enjoy a pigmale’s release.

Of course I was wrong. Ms Lee continued to up the ante and soon had me reach the impressive milestone of 40 days in chastity. However, while I was impressed with 40 days of chastity Ms Lee did not seem to be impressed in the least. She continued to increase the length of my chastity periods until I reached the unbelievable goal of 2 entire months in chastity for her pleasure. Even that did not seem to satisfy her and next I reached an entire quarter of a year, three months of unrelenting chastity! Once again this did not seem to quench Ms Lee’s thirst for seeing me endure strict and frustrating chastity sessions of ever longer periods and she continues to push me to endure longer and more challenging periods of chastity for her pleasure.

As my periods of chastity grew longer Ms Lee began having me attempt to achieve a release by anal stimulation alone. I have experimented quite a bit with anal play as I attempted to meet her expectation that I achieve a release without the use of my pigmale penis. At times I have come close, but I have not yet accomplished this for her. I know it will happen one day, particularly as I become so mindlessly desperate for release after months in chastity.

As I contemplated the likely reality that one day I will be capable of releasing without the use of my penis I began to wonder what Ms Lee’s intentions would be at that point. Would she see any point in ever allowing me a release with penile stimulation again? I suspected that she would occasionally allow this just so she could keep me off balance, never knowing when I might be allowed to play with her property. I also suspected that those opportunities would become more and more rare, as I know it would please her much more to have me only experience ‘hands off’ releases as a result of anal stimulation.

But what if she decided to cut me off permanently from penile stimulation? With the plethora of chastity devices available I have no doubt that one could be found that could be worn indefinitely. I have heard of some chastity devices that are attached via piercings in the penis and I have read stories where these piercings have been made permanent. Would Ms Lee ever subject me to such a fate? I’m not sure, but I have to admit that when my chastity periods begin to be counted in months I find myself fantasizing about this possibility.

I was hesitant to post this because I know that Ms Lee does not pander to my fantasies. I always have to remember that our unique relationship is based solely on her pleasure and my sacrifices towards that end. However, she has also made it clear that I should always let her know what I am thinking about and feeling so I thought it was important to express my thoughts about this. I doubt that she will reveal her eventual plans for me and I suppose that only time will tell. In the meantime I need to cease obsessing about this possibility and stay focused on what is important, the pleasure of Ms Lee.

 

 

My Ten Commandments

As Ms Lee has tightened her ownership of me an extensive list of her expectations has developed. I take these expectations very seriously as the consequences of failure are quite severe. I have earned the wrath of Ms Lee in the past for failing to live up to her strict expectations and the punishments she meted out are seared into my mind and cause me to scramble every day in a desperate attempt to please and satisfy her. I worship Ms Lee as my Goddess and her expectations are the ten commandments that form the focus of my daily life:

1) I am always to refrain from touching myself in a sexual manner without Ms Lee’s permission. My genitals are her property and are no longer available for my pigmale pleasures. I must beg Ms Lee for permission to touch myself, but only if she has given me permission to beg.

2) Every day I put my chastity sleeve on after taking my shower. It stays in place protecting Ms Lee’s property from any unauthorized touching or erections until I get ready for bed.

3) Every day I pick out a fresh pair of panties to wear, I no longer wear male underwear. I am also kept busy hand washing my panties on a regular basis, I would never dare present myself to Ms Lee in panties that were not in pristine condition

4) I must keep the area around my panties shaved and properly groomed at all times. There is never to be a single hair visible.

5) Every morning I conduct my morning worship session for about 15 minutes while properly plugged.

6) Every day without fail I make sure to contact Ms Lee in some way.

7) Every day I stretch during my exercise routine and meditate with Ms Lee as my focus.

8) On a weekly basis I post an update to the blog I maintain for Ms Lee.

9) On a monthly basis I send Ms Lee a monetary tribute as a demonstration of my devotion to her.

10) I apply myself to learning a variety of advanced study topics as determined by Ms Lee’s desires for my education and training so that I might better serve her. I am currently working on three areas of study:

A) I am learning how to provide professional quality pedicures accompanied by numerous pampering additions such as foot/leg messages along with the proper oils and lotions. I am searching out and studying web pages concerning how to give professional pedicures and I am also planning on getting a pedicure myself as soon as I find an opportunity sot that I will better understand the process.

B) I am learning how to milk myself anally, without touching myself. I am practicing this daily as well as searching out web pages with tips on milking yourself and proper tools. As I mentioned in my prior blog entry I suspect that Ms Lee has a substantial change in mind for my future ‘sex life’ once I master milking myself.

C) Self study – As time allows I am studying how best to please Ms Lee – what meals she likes, etc. I need to become on expert on pleasuring and satisfying Ms Lee

Feeling like a sissy

I’m not sure exactly when the change occurred but I’ve realized that my reaction to wearing panties has gradually changed from embarrassment to anticipation and excitement. I’ve always gotten hard and excited in response to the embarrassment I experience when wearing panties but now my excitement is also due to the pure pleasure I obtain from wearing them.

Recently I have had some discussions with Ms Lee because I have been struggling with admitting to myself that I am a sissy. I have been wearing panties and experiencing chastity for years but I had always felt like a man that was just experimenting with submission. Being told to wear panties was part of that submission and although wearing them got me excited and hard it was always due to the embarrassment I endured. But over time the primary reason for my excitement has shifted from embarrassment to the enjoyment I now experience from wearing panties.

I have become quite obsessed with my pretty panties and I have accumulated a large collection including a number of them with garters and frilly skirts. Plain panties are no longer good enough, I now search for frilly and sexy panties, preferably with a lacy garter belt. I think a primary driver of this obsession was due to the sexual starvation I endured when in chastity. I desperately craved any sort of sexual stimulation and I learned to enjoy the feel of my silky panties embracing my chastised genitals. Attached is a photo of one of my favorite pairs of panties, they include a lacy built in skirt and detachable garters.

Another obsession I had developed due to Ms Lee’s training involves my extensive collection of anal toys. Ms Lee requires that I conduct a morning Worship session every day that includes having my hungry rear stuffed with my anal plug. I have learned to enjoy the sexual stimulation I experience when my plug presses against my prostate. Just like what happened with wearing panties, I have come to crave my morning Worship sessions and the frustrating excitement I derive from having my anal plug tease my prostate. And just like with my panties, my obsession with my anal plugs makes me feel like a sissy. More information on my morning Worship sessions can be found in this blog entry – How i Worship my Goddess

Ms Lee told me that I should not be ashamed of anything that makes me feel good and she encouraged me to embrace being a sissy if that made me happy. While admitting that I was a sissy felt right to me I was still uneasy because of my preconception that all sissies are gay and that many of them wear diapers and act like little children or babies. While these things may be fine for other sissies they are not part of what I am. Ms Lee helped me to understand that I should not worry about the preconceptions of what is ‘normal’ for a sissy and that I should just enjoy those aspects that make me happy.

I am now putting Ms Lee’s advice into practice as I embrace being a sissy. I truly enjoy wearing panties and playing with my anal dildo and I am no longer distracted with the preconceptions about being a sissy that don’t apply to me. Once again Ms Lee has helped me to better understand my submissive nature. I am truly blessed to be owned by Ms Lee and I am very grateful.

A Ruined Orgasm

Fortunately for me, I was able to chat with Ms Lee the night before she expected me to try to milk myself at work again. She told me that I was lucky that I had gotten hold of her due to her busy schedule. She proceeded to tell me that during the course of one week she would be having sex almost every other day, as well as other pleasant events such as breaking in the dildo harness I had just purchased for her.

I was nearly insane with jealous frustration as I heard about her frequent sexual adventures, all while I was entering my third month in chastity for her pleasure. While she was free to have sex whenever she desired I was reduced to begging to be allowed to try to milk myself – without touching!

When I told her that she had my penis straining like mad against my chastity sleeve she replied:

good! put plug back in then & rock if you want

When I told her that I was now chastised, pantied AND plugged for her, she replied:

lovely!  rock away and see if you can milk yourself while we talk

As she proceeded to tell me more about her sexual escapades I could feel my penis straining even harder in my sleeve.  I told her that I felt like her cuckold, denied pleasure while she was free to enjoy sex all she pleased. Sne increased my frustration even more by telling me:

if you were here, i’d be taking you with me to my sex guy, binding you, & forcing you to watch & clean us both up, while chastised and plugged. i’d make you beg me to fuck you while you were on your hands and knees and his cock was in your mouth i’d make you keep your eyes open while you blew him so you could watch that cock in your own mouth  and yes, you would be plugged at both ends –  nobody fucks you but me, though

fantasize on that for a while. rock & try to milk yourself. you may touch only the head of your cock with only one finger.  i’ll wait

I desperately tried to milk myself, but even touching myself with one finger did not do the trick. Next Ms Lee told me:

Well, honey, i want you to cum, but i want it to dribble.  SO do this: keep chastity sleeve on, but you may touch. rock the entire time. when you feel yourself just starting to cum, STOP TOUCHING and let it finish on its own.  I’ll wait.

It took a while, but I desperately needed release so I masturbated like a naughty little boy, frustrated by the restraining chastity sleeve. I couldn’t achieve anything close to a real erection, but between two months in chastity and all the teasing I was enduring I finally was able to start cuming. The chastity sleeve had just the effect Ms Lee desired and all experienced was a pathetic dribble as two months of cum was released. No pleasure, no explosive ejaculation, just a constant dribble.

Ms Lee was pleased with my performance and chatted some more as she prepared to go out for the night. She increased my frustration as she told me she expected some more pleasurable sex that night. Then treating me like her little cuckold she told me:

Get some rest. You were a good boy for me and you’ve done well

Back after a long break

Due to a variety of issues and events, I ceased posting updates to this blog over a year ago. I am now ready to resume this blog.

I think folks may find my most recent experiences with Ms Lee to be quite interesting! I will start over the next few days by making ‘catch-up’ posts to bring everyone up to date.