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.

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.

A frustrating chat

About a week after I began wearing my anal plug on a daily basis I had an opportunity to have an exciting text chat with Ms Lee as she pleasured herself. The next morning I sent her this message reflecting on our chat:

Thank you so much for chatting with me last night. I know it is not easy on the phone. I hope that I helped you enjoy yourself and that you went to sleep with a smile on your face, thinking about my devotion.

I can’t begin to tell you just how frustrated I was after our chat. I thought I was going to lose my mind as I pictured you using your vibe as I described how I would love to rim you. And the fact that I was plugged and pantied for you at the same time just made my frustration that much more intense. When you told me you were coming I could feel my penis pulsing in desperation against my unyielding chastity sleeve.

The fact that I knew my own pleasure was to be ignored helped me to focus on yours. I worked very hard to please you by describing how I would rim you and use my fingers to excite you. I am becoming quite addicted to being devoted to your pleasure!

Attached are some photos I just took for you, showing me plugged, chastised and wearing the red panties with garters and skirt that I recently purchased. These panties tease me worse than any others! I don’t know I I am going to be able to endure all the teasing and frustration I am going to be subjected to today. Needless to say, you will always be on my mind.

Plugged, chastised & pantied for your pleasure,
In my 16th day of chastity,
and 34 days since my last pleasurable release

Released at last

As my week of unfettered masturbation (without release) neared an end I recieved a text message from Ms Lee that drove me crazy with frustration. My next message to her described my reaction:

Your message to me last night made me absolutely crazy with frustration. I got so hard and desperate that I got out my anal plug and slid it up my horny rear end. I then slipped my panties back on and got even harder in reaction to the tease they inflicted on me. I ground and rammed against the plug as I pictured you being rimmed and pleasured. I then began masturbating, trying desperately to stretch out the enjoyment, but knowing it was probably a losing battle. Your text message kept exciting and frustrating me, driving me to stroke even harder. Within a couple of minutes I lost control and exploded, releasing months of pent up frustration.

It was glorious to finally be able to enjoy an unfettered, pleasurable ejaculation. But at the same time I felt disappointment that I was not able to hold out longer and enjoy it further. I felt such an intense sense of release and pressure that I knew I would not be able to enjoy another release before the day ended.

Sure enough, I went to sleep last night without even trying to get hard again. I slept in quite late and had a number of chores to deal with this morning. I am now back in my panties and chastity sleeve even though there is no real need for the sleeve right now. I can feel some slight stirrings in my penis, but I don’t think it will be up to anything today.

I hope you had a great time last night, it was so awesome to get a text from you while you were being pleasured. I would love to hear more about it.

Back in chastity for your pleasure

Unfettered masturbation

After teasing me about being unable to release my chastity chains so I could masturbate, Ms Lee surprised me again:

go have an unfettered erection, an unfettered masturbation, and an unfettered production. Feel free to produce all week, in any way you so choose,  as often as you wish

 me: Really?

yes, really  🙂 it’s my reward to you for staying loyal

I was ecstatic upon hearing this and a few days later I sent Ms Lee this update:

I’ve also been thoroughly enjoying the freedom you granted me to play with myself as I wish for the remainder of the week. I have to admit that I have been wanking like a little school boy as often as possible. I had quite forgotten just how enjoyable it is to stroke my unfettered penis and experience unrestricted erections. I am on my knees right now thanking you for your generosity.

I also have a few other things I think I should admit to. The first is that I have discovered that it is almost a necessity for me to wear panties now in order to get fully sexually excited. In the last few days whenever I’ve tried to play with myself in the nude (like when taking a shower) I’ve found that it takes a while to really get hard and excited. I realized that I was craving the feeling of panties and as soon as I put them on I got rock hard and randy! I know that you are not fond of your boys dressing in women’s clothes, but you have instilled an incredibnly strong panty fetish in me. I have become quite adicted to wearing them and I beleive the reason is that when in chastity and not allowed to touch myself they provide me my only available sexual stimulation. When I am chastised and pantied I get aching hard ons due to the teasing inflicted by my panties, especially when walking and feeling them tug on my restrained penis.

One other admission is that every time I masturbate now I picture myself rimming and worshiping your awesome rear. The thought of rimming you to orgasm while I am chastised and denied drives me crazy! I get so excited that I have a hard time stopping myself from releasing. I also get excited when I think about you taking me with your strap-on, or having me milk myself with my anal plug. As soon as I think about anything else I start to loose my erection. Then as soon as I think about rimming you I get hard all over again. Are you training me to have an anal fixation?

And as I mentioned before, I am holding back on releasing becuase I am afraid that I will loose the sexual high that you have me on. I am so desperate and frustrated that it might take days after my release before I’m back to the point where I would enjoy playing with myself again. By then this week would be over and I would have squandered the opportunity you granted me.

Of course this means that my chastity (though unfettered) continues for now, with no pleasurable release just yet. I can’t beleive that I am stoping myself from releasing right away, but I have no idea when you might grant me an opportunity like this again. I need to savor and enjoy this freedom to touch myself as much as possible while I can. It has been nearly three months since my last pleasurable release and I know I’d better enjoy this while I can, since it might be a while before you allow me to do so again. Of course this means that my teasing and torment continues unabated. Even though I can now touch, I find myself in a position where I am still unable to truly let loose and just release at will. Your control over me is intense and deeply affects how I can react to the opportunity you granted me.

I apologize if I am rambling, but my mind and emotions are in turmoil right now. Once again you have knocked me completly off balance and I am scrambling to keep up. For instance – I have no idea if it is part of your plan, but I am beginning to realize that once you have me back in extended chastity I will be badly teased by the memory of how much I’ve enjoyed playing with myself, I had truly started to forget what I was missing and now you have reminded me.

In my 7th day of chastity for your pleasure, and now 83 days since my last pleasurable release

More begging

The very next day after receiving Ms Lee’s reprimand that I was not begging sufficiently on a daily basis I sent her this sincere message of begging:

I am quite concerned that you felt I was not begging sufficiently enough on a daily basis. I am truly desperate beyond belief and I’m constantly thinking about my need for a milking. I find it absolutely mind boggling that I am less than a week away from reaching two months in chastity for your pleasure. The main reason I have been able to control myself this long is the thought that my extended chastity pleases you. To endure my denial I have had to suppress all thoughts of my need for sexual pleasure and stay completely focused on yours, as I should.

I also find myself very focused on the thought of worshiping at your rear. I feel so submissive to you now that I feel a great need to demonstrate the level of my devotion in such a way. I hope you find it pleasing that I feel such an intense need. I would love to spend literally hours kissing and rimming your wonderful rear while using my fingers to pleasure your pussy. Since my pleasure is so often denied, and you feel my penis is inadequate, I would have to become an expert at pleasing you with my fingers. While I was rimming you I would concentrate on your pleasure, keeping myself tuned to your rhythm and desire. My tongue would tire, but I would continue. My fingers would tire, but I would continue. Your pleasure is what I would concentrate on, driving my tongue in deeper and keeping you excited.

Only after you were satiated would I then begin begging for my milking again. I need it so badly and I desperately need your permission for this. I am on my knees again pleading with you to consider my need and frustration. PLEASE, PLEASE let me releive the intense pressure in my balls! I need this so badly.

In my 55th day of chastity for your pleasure

Ms Lee’s pleasure

Although I was growing increasingly desperate as the legnth of my chastity increased I reminded myself that everything would be fine as long as I concentrated on Ms Lee’s pleasure. That is truly all that matters to me and I know that she will always see to my needs. On my 54th day in chastity i sent her this message:

I’m  excited that I was able to purchase the dildo harness for you. I hope you will be pleased with it, it looks really cool.

I’m also glad to hear that you have continued to enjoy my extended chastity. I am quite focused on your pleasure and I sincerely hope that the thought of my being in extended chastity, without even being able to enjoy erections, brings an occasional smile to your face.

You will see an example of how focused I am on your pleasure when I send you a photo of myself in today’s panties (my extremely skimpy pink & black thong). When I was getting ready to take the photo I noticed that I still had quite a bit of fur poking out from beneath my panties. It immediately occurred to me that you would not be pleased with my appearance, so I trimmed a good deal of the excess fur off for you. I hope you are happy with my newly trimmed look.

You may also notice in the photo just how frustrated and desperate I am at this point. My penis is constantly straining like mad against the tightly restraining chastity chains, keeping you always on my mind. Every time I feel my penis strain I find myself thinking that I should be worshiping you and thanking you. I am always compelled to think about worshiping at your lovely rear, demonstrating my submission and devotion. It would be so nice to reach around you and caress your awesome breasts as my tongue reached deeply inside you. I would play with your nipples until they were hard and excited, all the while thrusting my tongue deeper and faster. I wouldn’t stop until you were spurting and coming, and I wouldn;t stop then. I would instead pick up the pace and make you cum again. I would force my exhausted tongue to continue my worship as your pleasure became the center of my universe.

Right now I can feel my penis straining in futility as I contemplate your total control over me and my sexuality. I have passed the point of maximum desperation and desire for a pleasureable release. I understand that instead, the best I can hope for is that you may consider allowing me to milk myself to releive the pressure in my balls. I am back on my knees where I belong, begging you, pleading with you, to please allow me to milk myself. I can’t begin to describe just how desperate I am.

As I am begging, I find myself drawn back to focusing on your pleasure. I know I shouldn’t be so concerned about my own desperation. Instead, may I ask if there is anything else I can do that might please or amuse you?

In my 54th day of chastity for your pleasure

In reply, Ms Lee sent me this message:

Why am I not seeing you sufficiently beg on a daily basis?  You must not need it that much.

No fireworks for me

As I watched the fireworks on the 4th of July I felt a twinge in my balls every time there was a blast of sound and light. I couldn’t help being reminded of the fact that I hadn’t exploded in orgasm for nearly two months at this point. The next morning I sent this message to Ms Lee:

I hope you had a very nice Fourth of July holiday. I was thinking of you quite a bit last night. Every time I saw the fireworks explode I was reminded of my restrained penis that is doing nothing of the sort. I am absolutely astounded that I have now gone 53 days without a release. I would never have believed that I could go so long, but I am determined that I will not disappoint you and so I will not release until it pleases you. I also understand quite clearly what else I need to do for you and of course I will accomplish that as soon as possible.

Furthermore I understand that I will then have to beg quite convincingly in order to convince you how truly desperate I am for a milking. I have given up on dreaming that you might actually let me have an unfettered, full blown release any time in the near future. Instead I will devote my opportunity to beg to making sure I demonstrate my sincerity and desperation for a milking to release the pressure in my balls.

Although I am not allowed to beg for a milking at this time I do dream,of kneeling down and kissing your beautiful rear. I desperately want to please you by worshiping you in that manner, sliding my tongue deeply inside you as I rim you to orgasm after orgasm. It would be such a delicious contrast to have you enjoying such sexual pleasure, provided to you by your devoted boy who has now been in chastity for nearly two months for your pleasure. Every time you moaned in pleasure I would feel my penis strain against my chastity sleeve. I would concentrate on nothing but your pleasure, not expecting any sort of release in return. My opportunity to release depends solely on your whim and mood.

In my 53rd day of chastity for your pleasure

A Decision

While I was busy fashioning my milking chains and becoming anally obsessed I was not begging for my milking frequently or seriously enough. Ms Lee brought this to my attention with this message to me:

I’ve come to a decision on your begging with regard to your chastity, my love.

My decision is:

1)  Your begging was not sincere and no where near showing a need.

My remedy is:

1)  Get me that harness I emailed you the link for on a strapon, ASAP!  Contact me for an address when you do, because I may have moved or be near moving.

2)  Once I have the harness–in hand–I will then entertain again your begging me to be milked.

i realized that Ms Lee was absolutely correct and immediately replied with my apology:

I must apologize that my begging for a milking was not sincere enough and did not come close enough to showing a need. I assure you that after more than a month and a half in chastity for your pleasure I am experiencing extreme need and desperation. My penis constantly strains in futility against my sleeve and you are always on my mind.I will obviously be in chastity for a week or two more at a minimum. I understand that purchasing the harness for you is merely a prerequisite required before you will even allow me to beg for a milking again. And of course I will then have to do a much better and more sincere job of begging when I am allowed to do so again.While I am not allowed to beg for a milking at this time I would like to beg for forgiveness. I would like to get on my knees and apologize. While I was on my knees I would kiss your feet until you told me to stop. Then I would ask if I could humbly kiss your rear so I could demonstrate how sorry I am.

This would not be a sexually exciting (for me at least) rimming that I would perfrom, rather I would reverently kiss and worship your rear. My tongue would lick and caress without rest, at times touching lightly, at times reaching in deeply. If you chose to sexually enjoy this rimming I would continue until you were satisfied, without pause. At no time would I allow myself to get sexually excited or try to enjoy myself. My purpose would be to demonstrate my sorrow and to please you.

In my 48th day of chastity for your pleasure

Waking Ms Lee

As my time in chastity grew longer, my obsession with Ms Lee’s rear grew stronger. Every time I felt my deprived penis strain against my sleeve I would find myself thinking about rimming her.  One morning when my frustration was particularly strong I sent her this message:

It is early in the morning here and I am thinking about you sleeping soundly in your bed. As I watch you resting peacefully I can feel my penis stirring within my chastity sleeve. I have been in chastity for your pleasure for 40 days now and my penis attempts to harden in reaction to the slightest stimuli. Of course my sleeve firmly prevents me from enjoying such a pleasure so I am focused on your pleasure as things should be.

As I feel my frustration build I can’t stop myself from crawling into the bed with you and sliding beneath the covers. I would like to hug you, but in my desperate state I feel it would be more appropriate to worship your luscious rear instead. I lightly start to kiss your derriere and gradually move in closer. I let my tongue slip slightly inside your anus as I reach beneath you to feel your perfect pussy. I press my tongue in deeper and gently rub you with my hands. As I feel you begin to waken I press my tongue in more firmly and feel you push back against me.

As you move against me I become more excited and my penis strains even harder against my sleeve. I press my tongue in deeper and pick up the pace a bit with my hands. I lightly slide a finger inside you, but my tongue is even deeper inside your rear. I pull you into me as I begin rimming you in earnest.

Now you begin to stir and push against me even harder as I feel you begin to shake and moan. I pick up the pace even more as I feel your first orgasm build. I continue to rim you with my tongue as my finders push deeper inside your pussy, spreading your lips and massaging your clit. Even though my tongue begins to tire I don’t stop. Instead I rim you even harder and deeper as I feel another orgasm overtake you. My hands are getting wet as I feel you squirt. I would love to lick that up but my tongue remains firmly in your rear where it belongs. You are insatiable and my worship goes on and on until my tongue can continue no more.

I collapse in exhaustion as you stretch out in enjoyment from the multiple orgasms you just experienced. As I feel my penis continue to strain against my sleeve you tell me that I have been a good boy and that I have just earned myself the honor of being alllowed another day in chastity for your pleasure.

I hope you smile as you read this, thinking about me frustrated and pantied.

In chastity for your pleasure