This was the tale of a beautiful, stern and sensuous Mistress and her tiny dicked, collared servant who, at his own request, is kept locked in chastity. And Mistress Alegria was more than happy to oblige.

We have since moved on to the next phase of training and we would love all of you who followed us here to follow along with our new adventures.

The Cock Size has not changed though. It is still tiny!!!!

Thursday, February 25, 2010

Product Review - Phoenix Sapphire

littlechasteguy says:

In my never ending quest to find just the right chastity device for my needs I, with approval from Mistress Alegria, purchased a Phoenix Sapphire with a 30 mm cage. Three larger sizes are available, for those that are a bit larger. My needs include:

1.      Non-metallic as I pass through metal detectors daily
2.      Small in size to fit a very small penis and be easily concealable under street clothes
3.      Secure enough to prevent pullout
4.      Suitable for long-term wear in both comfort and ability to keep clean

I received my Sapphire just over a week ago, and as I had been a very good boy Mistress Alegria rewarded me by removing my CB-6000S the next day and allowing me to wear the Sapphire. (I’m not real patient, a character defect Mistress Alegria is helping me with.)

My initial impression upon opening the package was that it seemed bulkier than my CB-6000S. The ring is indeed significantly larger than the ring I wear with the CB-6000S. It is designed as one size fits all, with spacers to reduce the effective size for us smaller guys. The 30 mm cage we ordered is about ½ inch shorter than that of the CB-6000S, as hoped for to provide a better fit. The diameter is about the same as that of the CB-6000S at the “head” area of the cage. The CB-6000S has a smaller diameter along the shaft area, as the Sapphire is the same diameter the entire length of the cage. However, with the internal pressure pad installed the room inside the Sapphire is less than that of the CB-6000S, again providing for a nice snug fit on a rather thin penis like “Mistress Alegria’s”.

One minor drawback was that the package arrived without installation instructions. This required a trip to the Phoenix website to figure out how to install it. While only a modest problem, this could be easily overcome by simply including a one page instruction sheet with the device.

Installation required trying several different settings and spacer combinations to arrive at a good fit. I was pleasantly surprised at how comfortable the device is. It is lightweight and had no bothersome sharp edges or pinch points. The hinged pressure plate keeps “Her” little guy form bouncing around, enhancing comfort. And with the pressure plate installed as tight as possible without interfering with circulation or urination I found that the pullout inhibiting function worked as advertised. As I test by pulling backwards it tightened up, letting me know that I would soon be in great pain if I continued. The pressure plate also seems as if it will not cause the type of bruising and abrasions “Her” little penis experienced with the KSD-3 for the CB-6000S, although longer term wear will be required to fully assess this.

The cage of the Sapphire swivels slightly on the securing pin. This enhances comfort by allowing repositioning as my body moves and as the scrotum retracts when cold. The pinching encountered with other hard plastic, ball trapping devices does not seem to occur due to this flexibility. It remains to be seen whether focusing stress on this securing pin will result in durability issues.

Lastly, upon installing it was apparent that with the 30 mm cage being about ½ inch shorter than that of the CB-6000S, a better fit was achieved. This reduces the room for swelling when excited. Truth be told though “Her” little penis could probably squeeze into a 25 mm cage should one be available.

There were a couple of downsides we noted with the fit of the Sapphire. The large ring results in a bulkier package compared to the CB-6000S, and the need for internal spacers increases the complexity of installation. However, this bulkier package does not seem to result in any concealment issues, so this is more of an aesthetic issue. It remains to be seen whether this large ring will result in problems with activities such as bicycle riding. The other issue has to do with the urination slot at the end of the cage. It could be a little longer and more centered on the cage to allow for a cleaner stream and peeing while standing at a urinal. This should be a relatively easy improvement to make.

When I took my first shower while wearing the Sapphire I was pleasantly surprised with how easy it was to clean. There are plenty of well positioned access points in which to squirt fluids. Cleanliness should not be an issue.

So overall my initial impressions were quite favorable.

Then came my second night sleeping in the Sapphire. I awoke at about 5:00 AM with an unusual feeling of freedom and expansion. A quick check revealed that the cage had split along the seam around the diameter of the cage near the end. “Her” little penis was free!!! Thankfully there were no cuts. I had to quickly install the CB-6000S so as to avoid the wrath of Mistress Alegria.

It appears that the manufacturer produces the shorter cages by cutting down the longer cages and gluing them back together instead of welding. The glued joint failed.

I sent an email to Frank at Phoenix, notifying him that after less than 2 days of wear the device had broken. I asked for a replacement cage, one that had been reinforced in some manner. I received a reply about 24 hours later providing instructions for me to repair the cage with super glue, noting that if that did not work he would then send a replacement. So 5 days ago I glued it back together and have worn it for 4 days now. It has held together so far, although my gluing was not the neatest and thus the appearance suffers a bit. I had hoped for better customer service. While I understand the need to make a profit and that sending a replacement cage would be costly, in this case there was an obvious manufacturing or design defect that in my opinion should have been resolved by immediately sending a reinforced replacement cage.

At this point my opinion of the Sapphire is mixed. There are some great elements along with room for improvement. The hinged pressure plate is a great idea, and the reason I asked Mistress Alegria for permission to purchase the device. It works as advertised. The swiveling on the locking pin is also a great idea, improving comfort.

My primary concerns have to do with long-term durability. The seam failure after only 18 hours wear indicates that there is a serious quality problem to be resolved. I am thankful that I was not cut or pinched severely.

I would also like to see an American distributor with access to replacement/spare parts. The device took 10 days to arrive in Baltimore MD USA from New Zealand. If one of the components such as the cage, the locking pin, or the hinged pressure plate breaks I will not want to wait 10 days or so to get replacement parts. Keptforher.com stocks and sell replacement parts for the CB series of chastity devices and delivery only takes 2-3 days. While distributors would result in higher costs, to me it would be worth it for the improved customer service.

Lastly I’d like to see a smaller ring available. I’d also pay a couple of dollars for a more aesthetically pleasing device, as I am an exhibitionist and like to show off “Her” chastised little penis.

So my overall opinion after about a week is that Phoenix is off to a good start with the Sapphire. With resolution of the noted quality problem, and hopefully an improved distribution chain they should be quite successful.

We will of course provide another review after wearing for a bit longer term. We welcome any comments or questions.


Thursday, February 18, 2010

A New Pleasure Center for me

littlechasteguy says:

My Mistress is so wise. And as my Mistress She is also my teacher and mentor. Being somewhat new to this lifestyle, I sincerely appreciate having such a wise, caring, and strict Mistress. The trust I've developed in Mistress Alegria has allowed me to  journey deeper into my desired role as a chastised submissive.

Mistress Alegria has made me understand that "Her" little cock can on longer be a pleasure center for me. That is the only way I can, in the deepest recesses of my mind, accept total submissiveness to her loving guidance. "Her" cock is to be completely "Hers". However, in her infinite wisdom, Mistress Alegria has imparted to me that for her to remove one pleasure center without replacing it with another would not work. Nature abhors a vacuum. Failing to replace this pleasure center could lead to depression or resentment. While I derive great emotional pleasure from being allowed to serve her needs and desires, and love the compliments and rewards when a task is well done, I do enjoy some bodily/physical pleasure on occasion.

For this reason primarily, and also because she enjoys it, Mistress Alegria has begun me on a program of anal training. As her submissive I will learn to take the big strapon she likes using so much, and I will derive great pleasure receiving it. In fact, she tells me that in very short order I will no longer think about release for "Her" little cock as a reward for exceptionally good service, but that instead I will be begging for Her to fuck me with Her big strapon.

Over the last few months we've certainly engaged in anal play, as Mistress Alegria enjoys this activity and, being a good Mistress, She needs to know what makes me tick; where my response centers are. And she has certainly seen that I respond to having my ass played with. When she placed her small vibrating buttplug in my ass and turned it on I was in ecstasy, feeling pleasurable sensations I'd never felt before. When it was removed I begged for more. That experience and others have me excited and looking forward to this anal training program. I look forward to being pleasured by receiving a big strapon, even begging for it. The idea of enjoying being fucked by Her toys that are many times my size is so erotic to me.

However, up to this point I've only been able to handle relatively small toys in my ass without pain, not the big ones Mistress Alegria enjoys using; the ones she assures me with bring me the most pleasure once my body is properly conditioned. This pain is as much mental as physical. When I see Her big strapon juxtaposed against the little cock that formerly belonged to me I am intimidated. However, I've certainly seen cocks the size of Her strapon, and I've seen guys take them that size. With Her experience and wisdom in such matters I trust that She is absolutely correct regarding my eventual ability to do so as well and enjoy it. And so, as with "Her" little cock, I've willingly turned over my ass to Her for Her to do with as she knows best. She has taken ownership.

Recently we purchased a custom made, locking buttplug harness from Chained Desires. This harness was fitted so as to be comfortable, and is quite secure. Once locked on with a buttplug in place it cannot be removed with unlocking. Another nice feature is that the rings holding the buttplug in the harness can be replaced with larger rings to accommodate larger buttplugs.

As explained to me by Mistress Alegria the purpose of this harness is multi-fold. First and foremost I will be wearing plugs for many hours at a time to help condition my body to anal entry. As time goes on bigger and bigger plugs with be used until I can pleasurably accommodate Mistress Alegria's preferred strapons.

Another purpose of this harness is to reinforce Mistress Alegria's dominance over me. When locked in place  with "Her" little cock also locked it is a clear symbol that She owns all of me. With every movement I make I will be reminded that She is in control of even the innermost depths of my body.

Another benefit of this device is that it really looks good. With my matching collar and my chastity cage in place I am quite a sight in this harness (pictures will be posted soon). Being exhibitionistic in nature I look forward to wearing this new harness to public events, demonstrating for all the world to see that Mistress Alegria truly possesses all of me!

As our relationship has deepened over the past few months I've come to trust that Mistress Alegria truly has my best interests at heart. And She is so correct that I need to be wiped clean of all vestiges of my cock-centered attitude. Thus the switch to the mindset of a pleasure receiver rather than that of a pleasure giver, as "Her" little cock is unable to deliver pleasure. And to truly accept this reality to my deepest core, my physical and mental limitations regarding taking a relatively big strapon need to be removed. Thus the conditioning program.

And so the precess begins. I look forward with anticipation and I must admit some trepidation, although I know that Mistress Alegria, having my best interest at heart, will push me when I am ready to be pushed and will pull back a bit when needed as well. She is experienced at this and I trust Her probably more than I've ever trusted anyone before. I've certainly been more open with Her regarding my deepest thoughts than with anyone else.

I know I need more training to be a really good little subbie. And so the process continues .......

And I am happy!

Saturday, February 13, 2010

What's in it for Me?

Mistress Alegria says:

Prior to accepting littlechasteguy as my sub I set up a personal interview with him to determine whether he would be a good fit for Me. In earlier communications he'd already expressed that he wanted to have a strict Mistress who would enforce chastity upon him.

When he arrived and we began talking I was struck that here was an intelligent man who wanted to give up control of the most intimate part of himself. I was lost in thought as he filled me in on his life, ex-wives, jobs, and WHY chastity. Patiently I waited for the Real reason he chose to be kept chastised.

I quickly determined that littlechasteguy is a thorough submissive. This became apparent as he described his life and thoughts. I stored this away as a plus in his favor.

Finally came the reason for his goal of chastity. He mentioned that his cock was small, and that this resulted in relationship problems. To truly assess this statement I had him show Me. He was a bit nervous, just soft when he dropped his pants. He was not just small. He was Tiny! I made him erect for Me and, plain and simple, he was still Tiny! Now I knew.

I am curious one day to see him have sex with a woman, for My own amusement of course. Feeling for her I will of course have to have a real dick handy to finish the job, even if I have to strapon My lovely cock and finish the job myself.

Littlechasteguy your little cock seemed to have a lot of influence on you before you found out just how useless it was. To Me that made no sense. I thought you to be delusional at first. Did you not have eyes? Hence the constant masturbation. And the constant thoughts of what to do with your tiny cock. Then you discovered the final solution - Chastity. But being weak in mind and body you needed help.

Littlechasteguy, you could, had you wanted, come out of your self-imposed chastity. To Me at the time you were not in REAL chastity. I knew that your weak mind was still focussed on your little cock. I also knew that you remained focussed on orally pleasing women, something you could do all day if given the chance.

He needed someone to keep him in tow, to make him answer for his shortcomings, to make him a better man - one that would be an excellent submissive to a loving wife/life-partner/girlfriend some day. He needed to learn to be singularly focussed on pleasing his partner, and not concerned about his own pleasure. Seeing his submissive nature it was obvious to Me that he would take great pleasure in serving others, with the joy of service its own reward.

My littlechasteguy has nothing to offer as far as cock size goes. Chastity was wisely imposed. However, his service thus far has been nothing short of excellent. And it is obvious from his writings and our communications that he is enjoying this journey. However, My littlechasteguy it is apparent that your, or more correctly My, little cock still drives you.

We have a long way to go ......(and we will get there)

In future posts I will describe where we are headed on our journey and some of the guide posts that will be along our way. I look forward to reading about littlechasteguy's  thoughts and perceptions of his experiences. These writings will be a record of his transformation into the man he want's to be, completely devoid of thoughts regarding his inadequate cock and its pleasure, and single-mindedly focussed on bringing his Mistress pleasure in his areas of strength. It will be a joyous journey for all involved.

Peace,

Mistress Alegria

Thursday, February 11, 2010

What’s in it for me?

littlechasteguy says:

Several people have asked me, and I’m sure others wonder, what I as a healthy, physically strong, chastised male, gain from the chastity experience. I can assure you that for me the benefits are many, and well worth the challenges.

All day long at work I have to make critical and difficult decisions. I often need to confront others regarding their actions and job performance. I have no complaints regarding this role, as I chose it myself. I am also good at my job and am compensated fairly. However, it can at times be stressful when difficult decisions need to be made.

Also, in most of my relationships with family members I am required to make decisions. As the oldest son with a number of siblings, and as a divorced father of several daughters, I am relied upon to a great extent by family. Again, I have no complaints. I usually enjoy my role as the decision maker and arbiter of disputes.

However, as one who has to make tough decisions regularly, and be responsible for the outcomes, it is nice to not have to worry about other aspects of life. Since I have given total control of what is now Her penis to Mistress Alegria, the sexual aspects of my life are so much simpler.

No longer do I have to worry about pleasing women with my little dick. It has become a non-issue. As what used to be my little dick now belongs to Mistress Alegria, any such decisions or worries are entirely hers now. In fact, when I see a beautiful woman these days it never even occurs to me that I would like to fuck her. That is a non-issue completely, although I do often fantasize about being able to provide oral service. However, when those thoughts enter my mind I quickly remember that is not allowed without permission from Mistress Alegria. I am no longer a sexual creature except as directed by Mistress Alegria. That is very freeing.

Also, prior to giving complete control of my sex to Mistress Alegria I was a compulsive masturbator, jerking off at least once and often several times a day to porn. This occupied much of my time and energy. That is no longer a problem. It has been months since I masturbated, and on that occasion it was at Mistress Alegria’s direction for her amusement. Since I am no longer consumed with masturbation I have much more time for other, more productive tasks, such as serving Mistress Alegria and maintaining this blog.

Another benefit of enforced chastity is the physiological aspects. It is truly fascinating to observe and experience. After about two or three days I start getting very horny. With any free time my mind begins focusing on the buildup within me. As I reach about a week I am in a near constant state of horniness. By about 10-12 days I find myself leaking semen from my engorged balls. Of course regular tease and denial sessions only exacerbate all of this. By about 15 days I feel constantly ready to burst, feeling as if I could cum in my cage from the least little stimulation. Riding the train to work in the morning can be such sweet torture as her little weenie bounces around in its cage. I find myself forcing myself to focus on some reading material or work to break the mood. All of this is like being involved in a marathon foreplay session. And for me it is very enjoyable.

Another physiologic aspect that fascinates me is the mental changes that occur. The longer I am kept chastised the more submissive I become, and the more desperate I become to serve my Mistress. I can clearly see it, so I am sure Mistress Alegria sees it as well. As Mistress Alegria mentioned in her last post I was willing to walk to her house in the midst of a blizzard to serve her. I was not necessarily expecting to be allowed to cum, as I have given up complete control of that aspect of life, thus I do not have any expectations. I just wanted to serve and be in the presence of my Mistress, perhaps garnering a compliment and a smile from her. I love it when she tells me that I’ve provided good service. And she is genuine in her praise, as well as in reprimanding me when my service is lacking. Being an authoritarian figure in many aspects of my life, I very much enjoy my transformation into a true and complete submissive that enforced chastity engenders.

So, in short, enforced chastity is a freeing and transformative experience for me. My sexual inadequacies related to my tiny penis are no longer my concern. Mistress Alegria has freed me of that problem. And Mistress Alegria has provided me relief from the stress associated with being an authoritarian figure. While she values my opinion and requires that I be open and honest with her regarding my feelings and needs, it is nice to know that ultimately she is in control and will manage our relationship and activities. For me this works and I am very happy.

Saturday, February 6, 2010

Why own a Chastity submissive/slave?







Mistress Alegria says:
  
Frankly, until recently I really had no desire to. I had been active in the D/s Lifestyle for 10 years. I spent a lot of time learning, listening, watching, absorbing as much as I could, like a sponge. (Not the vaginal kind though, mind you. LOL)
      
I had heard through the years and thought it was yet another ploy to top from the bottom. I had seen Mistress after Mistress put their boys in chastity and seem more exhausted for all the trouble it cost to really keep them there. And not much service of any kind was given back to make it all worthwhile. For Me it was simply Women tying up their boyfriends packages to keep them from straying. I found no joy in that, nor excitement.
     
I saw real control of Mind, and not by a whip, by growing up at My home. To this day, in Her early 70's, you still bow to My Mother's will. From an early start We, all of the Women in My family, are born with that strength and that will. We run all of the households any man is privileged to have Us in, whether as wives or as girlfriends. In My family the women control the men, deciding when to have sex, and when not to. And chastity devices were not required. They were STILL in chastity.

Then my little chaste guy approached Me, requesting that I keep him locked in chastity. He showed Me his tiny penis, explaining that he was a compulsive masturbator and unable to please women with his little cock. He knew he needed to be locked up for his own good, and the good of the Females of our species.

We discussed expectations and together developed a contract, clearly stating those expectations. I was given total control of when (if?) what is now My little cock gets to release its spunk. And he consented to serve Me and My needs and desires, making My life easier.
  
My little chaste guy, I enjoyed reading your posting regarding your reasons for chastity. And you are absolutely correct when you say that what is now My penis is absolutely too small to ever bring pleasure to a woman, or a man for that matter. I am so glad you came to that realization all by yourself. It makes My job so much easier, since kept chaste you are much more compliant and willing to be trained to be the subbie I desire.

But all is not lost. I may someday let you penetrate a woman again, if I can find the right submissive woman who would consent to having what is now My tiny dick inside her. I would enjoy a good laugh as I unlock you after an extended period chaste, watch you struggle not to cum as she rolls one of your tiny “snugger fit” condoms on you, and then see how you struggle to bring her any pleasure before cumming yourself. And you know that if you cum before bringing her to orgasm you will be severely punished, most likely with a severe beating. And of course failure will mean never fucking again, for the rest of your life. But that might be your fate anyway.

Enforced chastity is an interesting dynamic in a D/s relationship, one I am truly enjoying. I love seeing the pleading look as I tease your locked up cock. I love how my chastised little subbie begs for release, even though you know none is forthcoming this time. I love seeing your little cock swell inside its tiny cage, bulging out the vents as in the picture posted on your picture page. I love knowing you will do anything I ask in the way of service, trying to please Me so I will be merciful. Most of all I love being in control. When you turned over control of your puny, useless penis, you gave Me control over all of you, body and mind. I own you My little chaste guy!

How long has it been now since your last release? Only eight days and you are already begging for My attention. You are willing to walk through the blizzard today in two feet of snow just for the opportunity to serve Me, on the outside chance that I will allow you release. How sweet, and na├»ve. I know you’ve been a good boy. I do appreciate your assistance in designing and building My new torture and interrogation chamber. But, My little chaste guy, you need to be patient. My little penis only gets to cum when I deem it necessary for my amusement. You gave it to Me. And I think I will wait a while. Perhaps I can go through the entire month of February without seeing My little penis squirt. I am curious to see what the readers of our new blog have to say about that. Good idea you had to solicit their input.

My little chaste guy, your chastised state has pleased Me to no end. It has made My training of you so much easier. I am sure that just a few months ago you never thought you’d be taking a spanking in public while chained to a cross. I’m sure you never expected to be paraded around naked in public, except for your little chastity cage that is. You probably never expected to assist Me as I played with another of My subbies. All of this is possible because you want to please Me so bad. And I didn’t even mention the cooking, cleaning, running errands, and serving other Mistress’s at My direction you’ve had the honor of doing.

And I have so many more treats in store for you over the next weeks and months. There is a long list of events we will be attending, you as My collared, little, chastised servant. Any day now the custom fitted locking buttplug harness you ordered will be ready. Then we can begin some serious anal training. You do remember that you also gave Me your ass to control as well, don’t you? And I want to get My ass thoroughly trained to take My favorite strapon cocks, the big ones (LOL). And I cannot wait to take you out in public with what is now My ass plugged and My little penis caged up and straining. Watching you squirm will be so delicious. Do you think I can make My little penis cum in its cage just from fucking you in My ass? I bet if we stay chaste long enough and fuck that ass hard enough it is possible. We shall see My little chaste guy.

And we will both write about our experiences from our own points of view to share with the world.

Peace,
Mistress Alegria

Friday, February 5, 2010

Why Chastity?

little chaste guy says:

I've been asked on occasion "Why chastity?" Doing a little self analysis this is what I came up with.

I guess my fascination with chastity is a derivative of my small penis humiliation fetish. It all started the first time I heard Aerosmith’s Toys in the Attic album, and heard the song Big 10 Inch. Like most guys my age (14 at the time), I measured my hard penis length with a ruler, finding that even if I press hard into my pubic bone I was more like 4 inches in length, not even half way to 10 inches. I figured that I was still growing and that it would continue to grow. (Never really did though)

In middle and high school I was always embarrassed about my size (or lack of size to be correct) when taking showers after sports or gym class. I tried to avoid others, without being too obvious, still thinking I’d be a late bloomer.

I had a few girlfriends in high school, and lost my virginity at 16. I had sex with two different girls in high school. My regular girlfriend was a virgin when we met. Looking back I don’t think she realized that I was small. The other girl was one who would get really stoned and allow sex with almost anyone, a real slut. She was usually too stoned to really be aware of anything.

After I left high school I joined the military. Being 18 and away from home I was able to start seeing porn regularly, as guys in the service do. Again I noticed that the guys were all bigger than me, but figured that they were oddballs regarding size. I was a bit taken aback once when my roommate exclaimed that he was bigger than the guys in the movie, figuring he was probably full of crap.

While in the military an incident occurred that again started me thinking in the recesses of my mind about penis size. One night a friend said his wife wanted to be part of a gangbang, and I was invited to participate. This all occurred before AIDS was around. There were six of us and we drew straws to determine order. I ended up being last. As the girl was banged we all watched. I became quite uncomfortable seeing that the other guys were much longer and thicker than me. I almost dreaded having to disrobe in front of them.

When my turn finally arrived it was as bad as I thought it would be. I was so self-conscious that I was only able to get half hard and as I slid my little penis into the stretched and sloppy pussy it was obvious that she could not feel a thing. She was nice enough, encouraging me to go ahead, but it was obvious I was ill equipped. I finally gave up, attributing my lack of performance to the alcohol and other substances.

Shortly after that I met my first wife. She was young and had had only one previous lover. My size never seemed to be an issue and the sex was good, if not the rest of our relationship.

After the divorce I had several girlfriends. One in particular taught me how to really perform oral sex to her liking. Rarely though did we have intercourse, usually I’d give her oral until she came several times, then she’d give me either a blowjob or a hand job. She never said anything about size, but looking back I am sure intercourse was not particularly pleasurable for her, thus rarely did we engage. I also had trouble cumming during intercourse, from what I now realize was a lack of friction. At the time I just thought I had great stamina.

It was during this period that the AIDS scare was going full bloom. I had one girlfriend who insisted that I use condoms for protection. Prior to this I’d never used them. We ended up breaking up because of this. I just hated them because they kept sliding off me and became too much trouble. At the time I guess I thought other guys had the same problem, but that they tolerated it to get sex. I also had trouble cumming in her pussy during intercourse. The only way I could cum was by really pounding hard for a long time. It was exhausting.

My second wife was pretty experienced and sexually adventurous. The sex was plentiful and seemed good to me at the time. However, there were some issues regarding my size. She was the first person to speak openly to me about it, pointing out that I was not very well endowed. I also couldn’t cum in her pussy during intercourse, until she discovered that if she put a finger up my ass and played with it I would squirt on demand. We soon had a routine. I’d eat her pussy to two or three orgasms, then I’d enter her and pound away uselessly until she felt merciful or tired and fucked my ass with her finger so I could cum.

We also experimented with anal. On occasion she would allow me to enter her ass. Usually I’d cum very quickly, as there was sufficient friction.

When I look back on those days I’m amazed that I wasn’t more aware of the problems caused by my small size. I would cum very quickly and easily when masturbating, or on those occasions where I was giving anal. However, even though relatively young, it was almost impossible for me to cum during intercourse. There were also a number of occasions where partners wanted to try certain positions, but because of my short length it was impossible. I’ve never been able to have intercourse while standing in the shower for instance.

It was during my second marriage that personal computers and the internet became available. Since I needed to learn to use a computer for work I bought one very early, and became an early internet user. I soon discovered online porn. As I surfed various adult news groups I discovered a whole genre regarding cuckolding, where wives whose husbands were rather small in endowment had sex with larger men. Often the husbands were allowed to watch, and sometimes participate in pleasuring the wife’s stud. I became fascinated, and the reality of my small size and inadequacy regarding intercourse began to sink in.

After my second divorce there was one long term relationship, and several of shorter length. The same sexual issues continued. I couldn’t cum during intercourse, condoms would fall off, and it became a chore. I found that I derived much more pleasure having a girl cum over and over again all over my face as I licked her to multiple orgasms. I also began jerking off more and more often to computer porn, usually several times a day. The more I did this the more I was drawn to pictures, videos and stories of women enjoying big cocks, often while their husbands or boyfriends masturbated their little penis’s.

At some point while surfing porn I encountered a story about a man whose little penis was so useless that his wife enclosed it in a chastity belt, controlling when he would get to cum. This set off a reaction in me. While outwardly controlling, particularly at work where I supervise a number of people, a submissive streak began to emerge. I fantasized about being subjected to such abuse due to my inability to properly fuck a woman.

During this period I also encountered a genre of porn regarding small penis humiliation, where women tease men regarding their small size often in public or group settings. Again an inner reaction was set off. As I read the stories and watched the videos and pictures of small endowed men being subjected to chastity and small penis humiliation (SPH) I became hooked, knowing that I was smaller than many of the men being chastised and humiliated.

I became fascinated with the supposed results of chastity, men becoming more attentive and docile, willing to do anything, no matter how humiliating, to be allowed to cum. I also read stories and reports of men, whose periods of chastity were stretched out to many months (sometimes being milked through prostate massage periodically), seeing their penis’s atrophy and become even smaller, often unable to even become fully erect. Some men seemed to find that when released after a long period of chastity they would cum before even fully hard. This fed into my already present sexual insecurities and desire to be teased and humiliated regarding my small penis. While my penis is around 4 inches long when hard and quite thin, (much smaller soft) I fantasized about being released from chastity in front of a group of women and being forced to masturbate in front of them as they laughed at my shrunken little weenie cumming before even hard. Then being locked back up and licking them to multiple orgasms.

Finally I took the step of purchasing a CB-2000, chosen because it was relatively cheap and short (2½ inches inside). I also began my efforts to find a keyholder, posting ads on Craig’s List and several adult web sites. After wearing the CB-2000 for a few days I found that it was pretty bulky, visible under much of my clothing. I also was able to pull my little weenie out the back when soft, defeating the purpose. I later located the KSD KeepSakeDevice from Kept For Her, which was effective at preventing pullout, although it does mean the device needs to come off every couple of weeks for a good cleaning.

However the problem of visibility under clothing still existed. So I bought a Mini-Birdlocked. While comfortable and easily hid under clothing it did not work well for me as it also was too easy for me to pull out from.

Next I purchased a CB-3000 and KSD for it, which while a bit longer than the CB-2000, is not as bulky and is shaped more like a penis, so if it shows (as it does in tight jeans or dress pants that aren’t pleated) it looks like an erection. I joined a chastity forum (Chastity Mansion) hoping to find a keyholder, in addition to my other web postings.

After a few months of wearing my CB-3000 periodically for a few days while seeking a keyholder I became frustrated with the lack of success. Living in a fairly remote area at the time there were not as many potential keyholders very close. Eventually I kind of gave up, when I met my last real girlfriend, Mary.

Mary was nice, and not at all dominant. I quickly realized that she was not likely keyholder material. But we did go out for several months, with the same old sexual problems. I would give her many orgasms orally, but could not cum during intercourse. Nor did she derive much sensation during intercourse. At home alone I’d jerk off while looking at SPH and chastity porn. One day I was lying in her bed naked when she walked in and got her first good look at my penis. It was soft and shrunken from the cool air, no more than a little nub pointing straight up maybe about an inch. I remember the disappointment in her eyes. She broke up with me soon afterward. I’m sure that my sexual inadequacies were at least partly the reason.

Soon after that relationship I decided that I would widen my range geographically to find a keyholder. Eventually, through a website devoted to chastity I met my first keyholder. She lived about an hour and 15 minutes away

However, this relationship did not work out. Looking back I blame myself mostly. Expectations were not fully discussed prior to her taking charge of my little penis. However, I did make it 17 days locked without cumming, my longest stretch since I first discovered masturbation at about 13 years old.

When the relationship ended I immediately began to masturbate. I came more than ever before. It just kept pouring out. I also noticed that my little weenie seemed smaller, although it did quickly recover its’ normal size. And I was so over-excited that I was not really fully hard when I came. The sensation of that tremendous orgasm made it all worth it, although I was a bit disillusioned regarding my initial experience. I decided to take advice I’d seen and prepare a chastity contract for future use. However, I knew at that point I was hooked on chastity and needed to find just the right situation and keyholder for me.

After looking for a long time, approaching many Mistresses on several adult web sites, and a couple of false starts, Mistress Alegria and I found each other. She has been in total control of my little penis for several months now. And it is wonderful!

Where our relationship goes is totally up to Mistress Alegria. She is in total control of what is now Her little penis, and thus she has near total control of me, body and mind. Being a good Mistress though, she does require that I keep her informed of how I am doing, any concerns I may have, and my desires. Our relationship has deepened and I love her being in charge of Her little penis, and thus ingrained in my heart and mind.

I hope this gives you a good view into my mindset and why I choose this lifestyle.

In future posts I will delve deeper into my fantasies and hopes for the future. And Mistress Alegria will post her thoughts and feelings regarding being in total control of what is now Her little dick. We will also post reviews of various chastity devices and describe real world activities we engage in. We also hope to hear from others with thoughts or questions. We will respond to any thoughtful comment or question.