Archive for the ‘Panties’ Category

Dressing up for Ms Lee

November 4, 2012

Some of the panties that I wear for Ms Lee came with garters attached. I am always concerned that someone might notice the bulges caused by the snaps at the end of the garters that are designed to hold up stockings. I find it quite embarrassing to wear panties with garters and I am always fussing with them.  During a recent conversation with Ms Lee I admitted that constantly playing with the garters had caused me to  wonder what it would be like to wear stockings. Ms Lee immediately told me to purchase some stockings and try them out.

This of course led to further embarrassment for me as I went shopping for appropriate stockings. I was wearing a pair of panties with garters attached as I was shopping and I was terribly concerned that the sales ladies might notice the garters under my pants. The garters do not show too obviously through my thick pants, but I am always extremely self conscious when I am wearing them in public.

When I got home with my new stockings I discovered just how much trouble and hassle it is to attach stockings to garters. I can’t believe that women would go to all that trouble just to impress men and my deprived penis kept straining against my chastity sleeve as I pondered the fact that it was now I who was struggling quite significantly, concerned about making sure my appearance would be pleasing to Ms Lee. I have to admit that I was very happy and flattered when Ms Lee told me that my new stockings looked nice.

Shortly after purchasing my new stockings I was chatting to Ms Lee about my experiences with them when she shocked me by mentioning that I should wear a girdle with them to hold my stomach in. I do have a bit of a belly and I had to agree when she said that if I liked looking pretty then I should wear something to hold my stomach in so I would look better. Her comment about looking pretty then caused me to ask if I could try a corset instead. I have always loved the way a women looks when squeezed into a lovely corset and I found myself wondering what I would look like wearing one. Ms Lee kindly allowed that I could try a corset as long as it did a proper job of holding my stomach in.

As we discussed the idea of me trying a corset Ms Lee told me that I should purchase a white corset to match the white stockings I had purchased. She also told me that she wanted me to purchase a pretty pink corset rimmed with black. This of course meant more embarrassing shopping trips as I made the additional purchases that Ms Lee required. I then discovered that wearing a corset was even more challenging than stockings, but I had to admit that I was thrilled when Ms Lee approved of my modified appearance.

I was further mortified when Ms Lee told me that I should keep myself shaved from the groin down since she did not like the look of hairy legs under stockings. Once again I had to admit that she was correct and I proceeded to shave myself as she expected, including my cock, balls and all around my rear. This was probaly much more trouble than a woman goes through when shaving her legs, but Ms Lee has exacting standards for me and I would not dare disappoint her.

I have been mentally struggling with the reality that I am sexually excited when dressing up in my pretty new things. I was concerned that I was responding to stockings and corsets like a girl might but Ms Lee put me at ease, telling me that I was reacting just like someone who is surprised to learn something about himself that he didn’t know before. She told me that just like it was with panties I would soon learn to enjoy wearing stockings and corsets. She tells me that this does not mean I am a sissy, but I continue to be embarrassed by how much I truly enjoy wearing pretty things for Ms Lee.

Below are a few photos I took of myself wearing my new pink corset with black trim and stockings (over my freshly shaved legs). If my readers enjoy these photos I might include some shots of my white corset in a future post.

My shrinking penis

August 31, 2012

Ms Lee seems to enjoy having my chastity chains severely tight. As I mentioned in a previous posting, she had me shorten them by a link each to correct me for having an unauthorized release. Initially this was to be for a period of a single week, but that was extended for another week when I asked if it would please her to extend my correction. This cycle was repeated until finally she told me that I should just extend my punishment thru the rest of the summer.

As Labor Day approached I sent her an email describing the torments that my tightened chastity chains had inflicted on me. Here is a copy of that email:

The last time I begged you to allow me to please you by extending the time I wear my tightened chastity chains you told me to do so until the end of summer. As the end of September approaches I realize that I am not sure if you consider Labor Day the end of summer, or September 21. Regardless, I am now on my knees begging you to allow me to continue enduring my viciously tightened chastity chains until the official end of summer on September 21.

Please do not grant my request unless it will please (or amuse) you. Although I have to admit that I am perversely excited by the pain of the tightened chains I can assure you that I am not enjoying my predicament. Although I have done my best not to complain to you, I am actually enduring a considerable amount of suffering. I have gladly done so because i desperately desire to please you and I am hopeful that I can continue to do so.

Below is a list of the various ways my tightened chastity chains are affecting me. Please understand that I am not complaining in any way or asking for leniency. I just want to make sure that you are aware of the full extent of what I am enduring in the hope that you might derive more pleasure from my situation.

– My penis is constantly crushed by my tightened chastity chains

– I have to sit down and pee like a girl because the chains are so tight that my pee continues to dribble out for a few minutes after I urinate

– By the end of each day my punished penis is raw and red

– At times my tightly chastised penis feels like it is being burned, I feel an intense stinging that will not quickly go away. When this happens I endure the pain by thinking about your pleasure

– Erections hurt even after I remove the chains at bedtime. The deep impressions inflicted on my poor penis continue to cause pain as if the chains were still in place

– I realize that the viciously tight chastity chains are conditioning me to prefer anal pleasure since any attempts to enjoy an erection are instantly corrected by the bite of the viciously tight chastity chains

– When my tightly chastised penis does attempt an erection it is barely able to achieve 4 inches in length. And of course it is restricted to less than an inch in thickness. This is quite humiliating and I am really beginning to wonder if my extended, severe chastity might actually be causing my inadequate penis to become even smaller than it already is

Once again I am on my knees begging you to allow me to continue enduring my tightened chastity chains. I sincerely hope it will bring you some pleasure and perhaps bring a smile to your lovely face.

In my 67th day of chastity for your pleasure,
my 67th day of enduring my shortened chastity chains,
135 days since my last pleasurable release,
and wearing my black lace panties with pink trim today

Although I would have gladly continued enduring my tightened chastity to please Ms Lee I was relieved when she told me that it would not be necessary to extend my punishment beyond Labor Day. That night as I removed my chastity chains before going to sleep I discovered that the effects of my viciously tightened chastity would continue. Here is the message I sent Ms Lee the next morning concerning this:

I hope your toes were curling in your sleep this morning as I thought about pleasing you with a long, sensuous foot massage. I would caress your lovely feet and rub each individual toe, kissing them as I moved on to the next. Before I started I would light an oil warmer so I could rub the warmth into your feet. I would also have candles lit and some of your favorite music playing to help you relax and enjoy the pampering. I would set out some plants and light some incense if you liked. I would always be trying to think of small new ways to maximize your pleasure.

I do hope you have a lovely morning and a wonderful day today.

I was also thinking of you last night after I removed my chastity chains as my desperate penis became painfully erect. I’m not sure if it got excited as a result of my touching it as I removed the chains or if it was the anticipation of the loosening of the chains (perhaps both). As I watched my penis becoming erect I once again thought it looked smaller than in the past. I was shocked when I took a ruler and laid it against my penis to check. As you can see in the attached photos, my erect penis is now less than 5 inches long! When I measured it a couple of years ago when I first fashioned my chastity sleeve I remember that it was a full 6 inches long. I can only assume that wearing my severely tightened chastity for so long has reduced the length of my already inadequate penis.

Even 6 inches is nothing to brag about, but it is incredibly humiliating to realize that my penis has shrunk so much smaller. Do you think it might get longer again once my chastity chains are loosened? I can’t imagine that adding back a single link to only four of my chains is going to restore a full inch back to my shrunken penis. I hope that in time I regain some of my lost length. But if it turns out that my penis has been permanently shrunk I sincerely hope that it provides you with some pleasure and satisfaction, or at least some amusement.

Severe chastity continues

May 30, 2012

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.

Four weeks in severe chastity

May 11, 2012

I have now been in chastity for four weeks and I continue to endure the viciously tight fifth chain that I added to my sleeve. I am becoming accustomed to it, but my penis is still raw and tender by the end of each long, frustrating day. At times the pain is almost unbearable, but the thought that my obedience might be pleasing Ms Lee enables me to get thru the days. Perversely, it excites me to realize that my suffering might also be pleasing to her. I am beginning to worry that Ms Lee might consider the fifth chain a permanent modification.

About a week ago I sent Ms Lee another photo displaying the effects of the fifth chain. Here is the message I sent with the photo:

I hope the photo I sent yesterday pleased you, displaying my determination to endure any amount of frustration or pain in submission to your expectations. As I near three weeks in chastity my desperation is mounting, but I have faithfully obeyed your no touching rule. The severe chastity inflicted by my fifth chain combined with the lesson I learned from your recent correction has enabled me to stay focused on your pleasure and satisfaction.

Attached is another photo I hope you might appreciate, displaying the effect of my exceedingly tight fifth chastity chain. The photo shows my firmly chastised penis as it attempts a futile effort to become erect. You can clearly see the four original chastity chains, but the new fifth one just behind the head of my penis is so tight that it is buried in the fabric of my sleeve.

Wishing you a lovely day.

In my 19th day of chastity for your pleasure,
Wearing my purple panties with pink waistband

The fifth chain

April 25, 2012

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

April 18, 2012

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.



March 7, 2012

As reflected by my abscense from posting, hectic times have continued for me. Fortunately, Ms Lee has continued to grace me with her attention and expectations, which helped me to continue on.

Ms Lee seemed determined to have me learn my lesson about the sexual frustration women endure, so I remain plugged for 2 entire months. Every day I had a firm reminder of Ms Lee as the pressure against my prostate caused my penis to strain in futility against my chastity sleeve.

Twice I was surprised when Ms Lee allowed me pleasuable releases. Ms Lee can be quite kind, depending on her mood and whim, however I am still averaging less than one release per month so far this year.

At the beginning of this month Ms Lee surprised me again when she sent me this message:

Hi and happy March!  So today as soon as you read this, I’d like you to remove everything, including your chastity sleeve.  Still no touching, but nothing, not even during morning worship. Nothing. No plug, no panties, no dildo, no touching, no nothing until I tell you otherwise.

At first I thought I would enjoy the freedom from the plug, panties and chastity, but soon I realized just how deeply Ms Lee has conditioned me. Every day I felt like something deep inside was missing. I felt naked without my panties & chastity sleeve and was tormented by unfettered erections that I was not allowed to touch. I reported my experiences to her:

I actually feel empty today without my anal plug. I find myself
clenching the muscles in my rear, but there is nothing to press
against. I miss the sensation of the plug pressing against my prostate
and exciting my chastised penis.

And I truly missed using my anal dildo this morning. After 10 days in
chastity the pressure is building in my prostate. I had grown used to
using the anal dildo to ‘scratch that itch’, but now all I can do is
clench my rear and feel my penis strain in frustration.

I know I will be thinking of you frequently today. Not because of the
anal plug in my rear, but perversely because it is missing.

Ms lee then surprised me again by responding:

Lol…wow.  Happened quicker than I thought.  Ok, experiment over.  Go ahead and panty again, plug up for worship, etc, etc.

Yesterday morning I gave Ms Lee a report on my return to panties & chastity:

This morning I also enjoyed using my anal dildo. However, as always I
was tormented by the long, slow buildup to the teasing edge of sexual
pleasure. I am never able to reach the point of true, intense pleasure
like I used to enjoy when I masturbated. Instead I hover at the edge,
close enough to know what I am missing, but denied any hope of a real

In my 15th day of chastity for your pleasure,
Wearing my red panties with garters

Another pair of new panties

November 22, 2011

A little while after I was ‘unplugged’ I returned to NYC on business and had an opportunity to go shopping for panties again. I sent Ms Lee this message regarding my shopping trip:

Yesterday I purchased my newest set of panties. I looked for a set with a skirt & garters as you expected. I had a bit of trouble finding a set similar to the red ones you like and was embarrassed to have to ask for help again. Finally one friendly sales lady suggested the skirt like panties I am wearing in the attached photos, but I was concerned because they had no crotch to them. We had to look around to find a matching thong from the same set. The photo titled WhiteBlkTrimThong shows me wearing just the thong, before adding the skirt/panties with garters.

I really hope you like these new panties, they tease me even more than the red ones! They are quite elaborate, with the seperate thong, double layered skirt and garters.

Unfortunately, I had neglegted to keep myself properly groomed in my pubic region, which Ms Lee observed when viewing the photos I sent to her. She then responded:

Does not look at all appealing with all that fur.  take care of it.

Of course I immediately did as she expected, trimming and shaving myself to a more acceptable presentation. I then sent her new photos of myself:

Attached are some photos I took this morning, after shaving and trimming my fur. I hope that my appearance is more pleasing now. I have to admit that shaving & trimming myself for you got me quite excited. I was actually in pain because my penis was straining so hard against my chastity sleeve..

Perversely, the pain just made me more excited, adding to my frustration. I haven’t quite reached three weeks in chastity, but my desperation is already extremely intense. Once again you have my hormones on a wild roller coaster ride. Please understand that I would never complain about my frustration, I am just hoping that it provides you some pleasure or amusement.



November 21, 2011

After 3 long weeks of wearing my anal plug all day long I reached the end of the month and was allowed to go unplugged. It was extremely difficult to wear the plug all day long, but I knew it pleased Ms Lee, so I endured.

I am always anxious to find ways to please Ms Lee. It seems that constantly being in extended chastity has instilled in me a very deep seated need to please her. On the surface, this would seem to be because I depend on her to determine when I am allowed sexual pleasure. But as I think about it, I realize that Ms Lee’s pleasure has become my own vicariously.  Pleasing her provides me with a strong sense of satisfaction and contentment.

Shortly after my ‘unplugging’, I sent Ms Lee this message regarding my experience:

Today is my second day without wearing my plug. I have to admit that I do miss it, although it is an incredible relief to no longer have to wear it all day long. At times it was quite exciting and enjoyable, and at those times I couldn’t get enough of grinding and rubbing on the plug. I would get so sexually excited and my penis would strain like crazy against my chastity sleeve. It was such an incredibly frustrating tease to be able to sexually excite myself, but be denied the pleasure of a release. I would just keep grinding and gyrating like crazy, thinking all the time of the awesome control you have over me and my sexuality. I absolutely thrill to be in submission to you and I thank you for having me. I do hope that my recent essay was pleasing to you and that you will consider keeping me on. I am now back on my knees, begging you to allow me to continue to be your faithful boy.

As exciting and sexually pleasing as wearing the plug was, it was also extremely uncomfortable at times and frankly quite inconvenient. Some times no matter how much extra lube I might use I could still feel a burning sensation that was very hard to endure. I also had to struggle at times with trying to walk and sit normally while stretched by the plug. In fact I am now back on my knees begging you to only have me plugged infrequently because it was such an effort and struggle. However, no matter how painful or difficult it was at times I was determined to complete the month for you, plugged, chastised and pantied because I wanted to please you and demonstrate my obedience and devotion.

I am also concerned that the constant plug wearing may have permanently stretched my rear. I do know that it steadily became easier to slide it in and I felt less and less stretched as time went by. I was thankful to hear that you didn’t think my penis would shrink from daily chastity, but I am certain that I have been stretched by the plug.

I also began to truly crave the sexual pleasure the plug was providing me. I get quite desperate for sexual stimulation when I am in extended chastity for you and I found that I could always excite myself by grinding on the plug. It was almost like I was allowed to masturbate again, but with no possibility of a release. Naturally this combination was incredibly frustrating, but I do think I was becoming addicted to the pleasure of the plug. I know I miss it right now. I can feel my penis straining against my sleeve and my rear feels empty as I gyrate uselessly in frustration. Are you trying to transfer my center of sexual focus from my penis to my prostate? If so, I think you may be succeeding!

I am also teased by the silky smoothness of the pink panties I recently purchased at Macys. The panties tease me just as the plug did, but they do not provide me the sort of sexual pleasure that rubbing against my prostate did. By the way, I am going back to NY next Wednesday and I’ll have a chance to go shopping at Macy’s again. Do you have any particular color or style of panties that you would like me to shop for?

Chastised & pantied for your pleasure,
In my 32nd day of chastity,
and 50 days since my last pleasurable release

A frustrating chat

November 19, 2011

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