My role in the pleasure of Ms Lee

Since she has taken me as her property I have been faithfully devoted to the pleasure of Ms Lee. I always keep my focus on pleasing her and satisfying her desires in any way I can. However recently I have been adjusting to the reality that Ms Lee has multiple lovers and submissives who pleases her sexually. As a result I have been struggling to understand how best I can please her – what role do I play, how do I best enhance her pleasure and satisfaction?

Ms Lee has made it clear that regardless of her other relationships she intends to keep me as her property and that my primary role will be to serve as her butler. This had also disturbed me as I discussed previously because I have had fantasies of serving as Ms Lee’s sissy maid. But Ms Lee does not pander to my pigmale fantasies and I now understand that dressing and acting as a sissy maid would only distract me from my primary purpose which is to please Ms Lee. I have now embraced the idea of being Ms Lee’s full time, live-in butler which is how I can best achieve my destiny as a service oriented submissive devoted to the pleasure of Ms Lee.

It is apparent that Ms Lee has a voracious appetite for pleasure, more than any one man could possibly satisfy. As a sexually hungry woman she has multiple men in her life. In addition to other lovers and boyfriends she has recently taken on a very talented lover who sexually pleases her perhaps better than any other man before. Naturally there is a role for real men to please her sexually. But it is clear that Ms Lee also has a need to own a male servant in every way – heart, mind and body. My goal and destiny is to be her devoted male servant. My heart is devoted to her pleasure in every way, happily sacrificing my own pleasure in order to enhance hers. My mind is devoted to learning the skills necessary to serve her properly and constantly thinking of ways to please and satisfy her. And my body is devoted to her pleasure also. Every day I wear my tight chastity sleeve which severely restricts any attempts to enjoy an erection. I also wear panties on a daily basis, which torments me with a mix of embarrassment and teasing frustration. And when it suits Ms Lee’s whim I may be required to wear my anal plug or subjected to physical punishment if warranted. I am thankful that she has given me the opportunity to be her male servant, devoted solely to her pleasure and nothing else.

While I am thrilled that Ms Lee is enjoying fantastic sex with her lover I have been wondering what role I might play in sexually pleasing and satisfying her. Of course when it comes to sexually pleasing Ms Lee there has never been any doubt that my own inadequate penis would be incapable of properly pleasing her. That is assuming I was attempting to sexually please her like a real man. Instead perhaps it is more appropriate that my penis pleases her in the only manner it is capable of – by remaining in faithful chastity, frustrated and forbidden to enjoy the sexual pleasure a real man enjoys at will. I am thrilled that in this unique way my penis can contribute to the pleasure of Ms Lee. While she obviously enjoys being pleasured sexually by real men, allowing them and their superior cocks to enjoy sex with her,  it is also clear that she appreciates having a male’s penis under her firm control, denied and frustrated while she freely enjoys all the sexual pleasure she deserves. I understand that it pleases Ms Lee to have my male sex suppressed or perhaps completely eradicated and I embrace this as my destiny since my only desire is to please her.

While my penis will probably play no role in pleasing Ms Lee (other than remaining in faithful chastity) there may be other ways I can sexually please Ms Lee. Perhaps rimming her is a role I could fill, assuming that she is not fully satisfied in that way by her lover or other real men. I would relish being the one who was devoted to pleasing her in that manner. It is also quite possible that occasionally it might please Ms Lee to have me orally please her pussy. I suspect she would enjoy experiencing multiple orgasms while I was firmly chastised, my frustration driving me to pleasure her to the utmost of my ability.

 I would also hope that Ms Lee would allow me to frequently pleasure and worship her lovely feet. Making love to her feet is another appropriate role that I could fulfill. I would hope that after treating Ms Lee to a professional quality foot massage and pedicure that on occasion she might allow me to worship her lovely feet as my reward for excellent service. Of course I am clear that such a privilege would only be an occasional reward granted if it suits her whim, I am certainly not automatically entitled to anything, no matter how hard I toil for her pleasure.

Since Ms Lee’s pleasure is my primary goal and purpose I am appropriately thrilled that she is being sexually pleasured by the real men in her life. Recently she informed me that she spent the day of my birthday being sexually pleasured and f**ked by her skillful lover. I have to admit that hearing that overwhelmed me with waves of submissive feelings – I was happy she was being pleasured and I was frustrated that I remained in faithful chastity while she and her lover were enjoying the sexual pleasure I willingly forego in order to please her. I told her that I sincerely hoped her pleasure was enhanced knowing that while she was being f**ked I was in chastity to suit her whim. I also told her that I hoped her lover’s pleasure was enhanced as he appreciated her new haircut which I had paid for (she looks so beautiful with her new hair style!).  It occurs to me that I should do whatever I can to enhance her lover’s pleasure when he is with her – because that in turn will enhance her pleasure.

I am sure I will continue to struggle as I adapt to the reality that Ms Lee is being well pleasured, both sexually and emotionally, by her lover and other real men. I am grateful that she desires to keep me as her property and I know all will be well as long as I continue to focus on nothing but her pleasure, avoiding the distractions that worrying about myself would cause.

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.

Return to Worship

After weeks of faithfully abiding my Ms Lee’s no touching rule I am frustrated and quite desperate. Being unable to satisfy my intense desire for self pleasure I found myself ever more focused on Ms Lee’s pleasure. I began to ask her if there was anything I could do to please her and she responded by telling me to resume my morning worship sessions.

My morning worship sessions seemed designed to optimize the frustration that I endure as the Property of Ms Lee. Before I begin my worship session I must have my anal plug in place. My deprived penis begins to get hard as soon as the plug begins to invade my tight rear and by the time the plug is fully in place my penis is rock hard. I get quite excited due to finally getting to experience some sexual stimulation but it is extremely frustrating since I am still prohibited from touching my penis. The pleasure I derive from rubbing the plug against my prostate is nowhere near as immediate or intense as what I used to enjoy when I was allowed to stroke my penis. Instead I find myself ramming the plug in as deep as possible while I gyrate like mad, desperately trying to amplify my greatly reduced pleasure.

While I engage in my desperate dance of frustration I focus my mind on Ms Lee, concentrating on her pleasure. It is extremely difficult at this stage to resist the urge to touch myself but I remind myself that it pleases Ms Lee to have me obedient and frustrated. I continue to meditate on Ms Lee, thanking her for taking me as Her Property. I find myself almost falling into a trance as my focus moves back and forth between my intense frustration and my gratitude to Ms Lee.

My morning worship sessions are an effective tool for enhancing my devotion to Ms Lee. They also greatly enhance the desperate frustration I endure but hopefully that pleases Ms Lee which is all that matters.

Severe chastity continues

About the time that I reached 5 weeks in chastity Ms Lee took mercy upon me and told me to take a week off from wearing the viciously tight fifth chastity chain. I was extremely thankful for her generosity and enjoyed an entire week free from the intense pain inflicted by that chain whenever my deprived penis attempted to become erect. The remaining four chains were still quite effective at preventing anything approaching a full erection, but without the nasty bite that the fifth chain inflicts.

When my week of relative freedom was up I sent Ms Lee this message, asking at the end whether I was to return to the harsh control of the fifth chain:

As I continue my seventh week in chastity my desperation is reaching incredible heights, but when my frustration becomes too much I remind myself that my extended chastity is an opportunity to please you. I love pleasing you with extended chastity, but my hormones do begin to rage against the denial.This morning during Worship I was grinding against my huge Worship plug as hard as I could, but was unable to achieve any sort of release. I believe I have enough built up pressure inside that I am ready to try milking myself with my vibrating anal dildo again. I am not sure if you will consider my chastity period extended enough yet, but I think I will be begging you for permission to use it before long.

I also had an incredible struggle getting my chastity sleeve on this morning. My greedy penis kept straining against the sleeve as I slid it on. I am insanely horny this morning and my penis will not stop attempting to get hard. Every chain was another huge struggle and it took quite a while to get all four chains onto my unruly penis. Without the extra tight fifth chain my penis continues to bulge out between the four chains, but is unable to achieve anything near a true erection. I have enjoyed a week without the daily suffering inflicted by my fifth chain, but I think the week is about up, so I am now on my knees asking you to let me know whether I am to return to the extra security enforced by the fifth chain.

In my 43rd day of chastity for your pleasure,
wearing my pink panties today

I could have just resumed wearing the fifth chain without asking, but I was hopeful that Ms Lee might extend my period of freedom from that nasty fifth chain. Her reply was short and clear:

I do like that fifth chain.  Time to put it back on.

I felt like a condemned man when I received her response, but I have to admit that perversely, my penis twitched in desperate frustration as I read it. It has now been three days since I resumed enduring the intense restriction of the fifth chain. Once again my penis is raw and sore at the end of each day of painful chastity, but my only concern is for the pleasure of Ms Lee.

Return to regular Worship

During the first week of enduring the viciously tight fifth chain I kept expecting Ms Lee to take pity on me and tell me I should stop wearing it. Gradually I came to the realization that she probably preferred seeing me this way, secure in my firm chastity and suffering for her pleasure. As I began my second week of secure chastity I sent Ms Lee an update on what I had been experiencing:

I don’t want to spend too much time boring you with my sexual frustrations, but I do feel I should briefly let you know how I am doing. I am now well into my third week of chastity combined with no anal stimulation at all – no plug during Worship or at any other time. I have also been enduring my extremely tight fifth chastity chain for over a week now. Due to my extended chastity and denial of stimulation my penis is frequently throbbing in desperation. Every time that happens my chastity brutally prevents the feeble attempts at erection and my only reward is the pain of the chains digging in. By the end of the day my penis is sore and red from its futile struggles. However, the pain and frustration is worth it if the result is your satisfaction and pleasure with my faithful obedience.

I think I will be on my knees begging for the anal plug again quite soon.

I have to admit that I was relieved when I received this reply from Ms Lee:

Resume your plug & regular worship now.

The next day I gave Ms Lee a report on my return to regular Worship using my plug:

This morning it was so nice to be able to use my Worship plug, I have felt so empty! It was a bit difficult getting it in as my rear as not been stretched lately, but it felt wonderful once it was all the way inside and rubbing against my prostate. All too soon I was gyrating like mad, enjoying some sexual stimulation at last. I was shocked when I realized that I may have been more desperate for anal stimulation than stimulation of my penis. Perhaps because it is the only type of sexual pleasure I am usually allowed anymore.

Also, attached is a photo that shows my penis after I removed the sleeve at the end of day yesterday. There are some blood marks that are not too visible, but I think they demonstrate just how tightly restrained my penis has been for the last week.

Please understand that in no way am I complaining or looking for sympathy. I just want to let you know that I am so determined to be your obedient boy that I gladly suffer my frustration and desperation.

The fifth chain

For a few days now I have been enduring an extremely tight fifth chastity chain that I have attached to my chastity sleeve. This new chain is quite painful at times, stinging as is bites into my firmly restrained penis. However, as I explain below, I feel this increased level of chastity control is necessary and will insure that I adhere faithfully to Ms Lee’s no touching rule.

Here is the message I sent to Ms Lee explaining why I felt I needed the additional chain:

I hate to bother you again and risk annoying you with my trivial frustrations, but I feel I should let you know that my level of desperation is reaching even more incredible heights. For a year now I have been experiencing extended chastity periods and my level of frustration is nearly unbearable. My penis seems extra sensitive now and my panties are teasing it like crazy. I can’t stop straining against my sleeve and I frequently find myself grinding my rear against my seat. As you expected, I have not been using my anal dildo or plug during Worship and my rear is feeling quite neglected.

I have been so desperate lately that I have been worried that I might be tempted to touch myself again. I can’t conceive of disappointing you in such a way so for now I have added a fifth chastity chain to my sleeve. The four I normally use have allowed my penis to become partially erect between the chains which is driving me crazy with sexual desire. The partial erections result in my poor penis looking like some kind of restrained sausage and they are quite distracting.

To more firmly restrict my naughty penis I used one of those milking chains I had fashioned previously. It is a couple of links shorter than my normal chastity chains and digs in quite painfully whenever my misbehaving penis attempts a partial erection. I secured it at the end of my penis, right behind the head. So far I have found this addition to my chastity to be quite effective, with the tempting partial erections now eradicated (although my penis continues to strain frequently against the chastity chains). My penis is now very firmly restrained and in full submission to your will. I will continue to wear this fifth chastity chain until you tell me otherwise.

A just punishment

Recently Ms Lee gave me a very firm reminder that I must always be a good, obedient boy for her. My lesson began when I briefly lost control of myself and allowed my pigmale desires to get the better of me. One morning during Worship I was so frustrated and desperate that I found myself lightly rubbing my penis. It was futile since I was wearing my chastity sleeve and I stopped when the pain of my penis throbbing against the chastity chains became too great. I then felt quite guilty and dutifully reported the event to Ms Lee. I expected her to be disappointed with me and thought that she might punish me, but I had no idea just how severe her punishment would be. This is how I reported my transgression:

I’m glad that it does not bother you that I constantly tell you about my frustrations and desperation. It drives me crazy that you did not even respond to my begging to be allowed to wear my plug. I remember how deviously pleasurable it was to experience the plug filling my rear and teasing my penis so much that it would strain uselessly against my chastity sleeve. It frustrated me badly, but like now I was so starved for any sort of sexual stimulation that I gladly endured the discomfort.

This morning I once again gyrated like mad as I thrust my anal dildo in my rear as I attempted to milk myself. Once again (possibly due to recent stress) I was unable to produce anything more than a slight dribble. And right now I am on my knees begging you for forgiveness because during this morning’s session I gave into temptation and touched myself while using my anal dildo. I did not masturbate, but I did rub myself with a couple of fingers. I had to stop when the pain of my chastity chains digging into my penis became too much, but I feel quite guilty about this wanton behavior ( I don’t use my sleeve to protect my penis while milking myself and it doesn’t usually get too hard then anyway, the focus is on my rear and prostate).

I am now safely in my sleeve (and chains), but I continue to squirm in my seat in desperation while my rear clenches against emptiness. I am so frustrated, and so sorry if I disappointed you.

In my 46th day of chastity for your pleasure,
Wearing my first pair of purple panties today.

Ms Lee’s displeasure with me was quite clear in her response:

I am very disappointed.  In all the months and years we’ve known each other, you’ve not disobeyed me.  I am not happy about being put into this position.  Do the following and respond to this email acknowledging your submission to my wishes:

(1) 1500 word essay stating the importance of obeying and being a good boy.  Due Tuesday night, absolutely no extensions or exceptions.

 

(2) Send another tribute, immediately.

 

(3) Punish your rear and your penis with a tool of your choice.  I want your rear black and blue and your penis very well-striped.  Send pictures and I will let you know if sufficient.

 

(4) No touching, no plug for morning worship, just chastity, until I tell you otherwise.

 

Back to ‘normal’

Lately I have been distracted by some personal issues as well as a backlog of chores left over from the end of year holidays. Fortunately things have recently returned to a more ‘normal’ state of affairs. I commented on this in a message to Ms Lee:

Now that things have somewhat returned to ‘normal’, I was able to
enjoy an unrushed Worship session this morning, followed by another
attempt to milk myself. While I was unable to produce anything I found
it pleasurable (in a different way) just to be able to relax and
experience the sensation of rubbing the anal dildo against my
prostate. The sexual pleasure was nowhere near as intense as normal
male masturbation, but nevertheless I find myself looking forward to my
milking sessions.

I am still experimenting and learning how to adjust to deriving my
sexual pleasure solely thru my rear. Lately I’ve been using my anal
muscles to grip the anal dildo during my milking sessions, hugging it
as it slides in and out, trying to pull it in deeper and harder. Just
thinking about that has me doing the same thing right now with my anal
plug, which is quite frustrating, causing my penis to strain against
my chastity sleeve.

In my 14th day of chastity for your pleasure,
my 12th day of being plugged
and wearing my pink panties today

An early Christmas gift

While I was marking my penis for Ms Lee she graciously agreed to allow me to purchase an anal dildo for myself as a Christmas gift from her. She was even kind enough to inform me that I did not have to wait for Christmas before trying out my new toy.

I eagerly visited my local adult store to shop for my Christmas gift from Ms Lee. After looking over the available anal dildos I selected a nice red vibrating model that looked like it could help me deal with my ‘problem’. I have attempted to milk myself with a regular anal plug, but I have been unable to succeed. Due to Ms Lee’s no touching rule it is quite difficult to reach a level of sexual excitement necessary to achieve a release. Using the anal plug  just gets me extremely frustrated as I near the edge of a release, but am unable to reach it.

I waited until after my Worship session the next morning before I tried out my gift from Ms Lee. I wanted to use my Worship session as an opportunity to properly thank Ms Lee for her gift before I opened it up. This was also a nice ‘warm up’ since my Worship session involves putting a 2 inch wide anal plug up my rear.

Once my Worship session was complete I removed my plug and inserted my new anal dildo. The anal dildo is custom designed to rub up against my prostate and has a variable vibration feature. Here is a photo of my Christmas gift from Ms Lee:

The two inch anal plug I used during Worship opened me up quite nicely so that the anal dildo slid in with no trouble. I located my prostate and pressed the tip of the anal dildo against it and then turned on the vibration. The sensation was incredible as I felt my prostate react to the stimulation. I started grinding and pressing against the dildo, trying to increase my excitement.

I soon found that this sort of sexual stimulation was quite different from normal male masturbation of the penis. Instead of rapidly reaching a peak of excitement I had to work at it, gradually building up my level of sexual excitement.

I also had difficulty finding the right position to achieve maximum excitement. I first positioned myself on my knees, but it didn’t feel like I was getting in deep enough. I tried lying on my side and found that I could more easily reach my prostate and began gyrating like mad. But even this was not enough and my frustration grew. I wanted more! Finally I laid on my back and spread my legs, arching my back upwards. This seemed like the best position to allow maximum penatration and my gyrations increased.

As I bucked and ground against the anal dildo I realized that I was positioned just like a woman that was being penetrated by a man. I was also responding in the same manner, thrusting up and back in an attempt to increase my excitement.

I also realized that the sexual excitement I was experiencing was quite unlike that a man normally feels. I did not enjoy a strong erection and a rapid build up to the point of explosive release. Instead I experienced a maddeningly frustrating, slow build up, which caused me to thrust and gyrate ever faster. But no matter how hard I tried, there was to be no joyful, explosive release for me.

Eventually I also realized that my penis was leaking what seemed like pre cum. I was surprised at first because I expected to feel something when my penis released fluid, but there was almost no sensation at all. The fluid just slowly leaked out, with no pleasure or satisfaction achieved at all.

Finally I collapsed in exhaustion, unable to grind or gyrate any more. I looked at my belly and saw a small pool of nearly clear fluid, nothing like the thick blobs of semen that I would produce from a normal masturbation. I also did not feel anything like the normal satisfaction that masturbation provides. Instead I felt frustrated and deprived.

I also soon found that while the pressure that my extended chastity had produced was now eliminated, my frustration and desperation was unabated. If anything I was even more frustrated and desperate than ever.

Begging to be plugged

Today is my 48th day in chastity and my desperation is reaching new peaks. My deprived penis is now almost constantly straining against my chastity sleeve and I am finding it quite difficult to concentrate on anything other than my submission to Ms Lee.

This morning’s Worship session was another exercise in extreme frustration. I am now badly craving my daily opportunity to ram my huge Worship plug up my rear in a pathetic attempt to experience what little sexual stimulation I am allowed. Once again I gyrated like mad on my plug and exhausted myself by the time my session was completed.

As always I ended my session by giving thanks to Ms Lee for keeping me on. As I was doing so I resolved to ask her if it would please her to allow me to once again wear my plug for an entire day. At this extremely extended point in my chastity I don’t know if I could stand the teasing and frustration that wearing the plug all day would inflict on me, but my desperation is getting the better of me.