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.