The First Stretch

I've posted some here already and I have decided it would probably be more appropriate to post in this particular subforum.

Here are some of the original posts:

http://www.chastitymansion.com/forums/index.php?threads/newbie-saying-hi.16067/#post-140872

Before going into the particulars about my experience in chastity, I feel I should provide a bit of background about myself. I'm a big 22 year old, 6 ft 5, 220 lbs. Never been all that into exercise, so I have a pretty average body. I found out that women were sexually interesting when I saw an ad for Girls Gone Wild on TV when I was 13; and realized that I liked men when I messed around with a friend at age 15. Despite essentially getting blowjobs on demand for about a year, I didn't really start to define myself as bisexual until my college years. Despite plentiful opportunity, I never really engaged in any sexual relationships since high school and don't really have much desire to until I more or less get on my feet in terms of stable income and a career.

Unlike some other things in my life, I can trace my kinky interests to a couple of distinct points. My fuck buddy in highschool had a bit of an underwear fetish, something that transferred over to me. Once I got aware of kinks actually being a thing, I had some fun until I stumbled across some photos of Taylor St. Claire's ruined orgasm and t&d work one summer morning when I was fifteen. Something switched, my fantasies took a turn towards T&D. Since then, I became aware of the wide world of chastity and TD and have enjoyed the media that world has to offer. Beyond numerous ruined orgasms and the occasional week long period of teasing, my interests remained fantasies until recently.

I had mulled over the idea for a while, but I finally took the plunge and bought a few sex toys, namely a fleshlight and a very good chinese knockoff of a CB-6000S. Once I clicked it on, fantasy became reality. I know now why people are into this. The constant feeling of neediness, arousal, and submission is really incredible, I am now hooked.

The last week was intense. What started as essentially wank fodder got very real by day three, I've felt a sort of horniness that I didn't really know existed. I faltered a bit, almost cumming during a teasing session, but I held out the rest of the week. During a hormone fueled frenzy earlier in the week, I bought a Rude Boy vibrator. Being an anal virgin, this sort of bold step seemed to only make sense at the time. After a failed attempt at using it on Friday, I more or less put it away, only using it to tease my locked up cock a bit. By Sunday night, however, lockup was getting to me, as I was starting to feel the symptoms of prostate congestion. So, I bit the bullet and decided that a milking was in order. It took a bit of effort, but I managed to get the vibe in. I played around with it until I found my prostate and upped the speed a bit, as well as fucking myself with the toy. I felt what I had heard to expect when you got milked (feeling like you had to pee), so I worked the toy with a bit more speed. A dribble of milky fluid flowed out of my semi-hard cock, followed by three forceful spurts of cum onto my shirt. Now drained and feeling rather slutty , I cleaned up and went to bed, though the back of my mind was still screaming that I hadn't actually cum. Even though I stroked a bit yesterday, I hadn't cum at all. So, back into chastity I went.

So, now that the wall of text is over, I sit at a crossroads. I have been feeling slutty and horny all day (did I mention I bought a dildo today? ), but I am still locked up. Honestly, that is the only thing that feels right.
However, I am having a bit of a problem figuring out what I am going to do. I am intending to hold out for the next three weeks, but I don't really know how that period is going to end.

Regardless. I got me some rules:

-No cumming until November 2nd, so no ruined orgasms.

-I will only be released from chastity for cleaning and teasing sessions

-I get three teasing sessions per week, each one limited to ten minutes. I can fool around for longer, but I have to be locked. Again, no cumming. During these sessions, I can do whatever I want, from jerking off to stroking with the fleshlight. However, I cannot fuck the fleshlight. The 30 minutes of teasing time can be done all at once or divided up.

-I get two milking sessions per week, no time limit on them. However, I cannot jerk off when actually toying.


So yeah. I hope this read was relatively enjoyable. I am looking forward to any imput as to how and when I should conclude this teasing session.

 

Guodor: Probably. I am waiting until friday for another milking session. I need a baseline for future comparisons.

 

So my scheduled release day is next Monday. Yay.

However I want to make it somewhat difficult for myself. I am intending to fuck my fleshlight to completion, and then probably eat it out (not a deterant lol).

I am thinking of giving myself only a minute to cum. For every day or week I remain chaste beyond this date, I get an additional minute or 30 seconds. However, once I decide to fuck it, I can't go back. If I don't cum in the allotted time, I have to stay chaste for another month.

That sound good? Any suggestions?

 

Well, as it is November 2nd, I have been chaste for one entire month. That means it is time for some fun:


It's all eaten out and ready to go, just a matter of unlocking myself.



A little teasing first.



I'd only been at this about 2-3 minutes, my cock was crying.



Just a little bit more teasing...

All I had to do was get down on the floor and hump away, I would have one full minute to cum. But, if I waited until Wednsday, I could have another thirty seconds for each day I held off. I would kind of like to enjoy my fuck session, and the idea of not being able to finish and going back into lockup was a bit stronger than the urge to cum.

So...:



I showered off, (played with it a little ), and then locked it safely back up.

It is gonna be a long two days, but the end result should be nice. Unless Kitty_Mischief or someone kidnaps me.

[Edit by SubVerity - This post may seem a tad disjointed as images have been removed]

 

Ok

 

Sorry about the photos.

As for Wendygirl's comment. As definition of chaste, I would personally consider that having not orgasmed. I fool around from time to time, but I don't cum.

 

Wasn't happy with my last explanation, the time limit to edit the comment expired, so I'll try and give a bit more depth.

I have heard multiple definitions of chastity thrown around in this particular kink, one is no sexual activity, the other is no orgasm. In all honesty, if I were locked up by a KH and not taken out and teased, it more than likely wouldn't bother me all that much. I enjoy tease and denial, I some sort of sexual activity to keep it interesting. That can mean jacking off or playing with a fleshlight; something that will give me something to fight with myself about. That inner turmoil and deliberately being denied release is what I get enjoyment from. I haven't cum in the conventional sense this month, that is what I consider chaste. Other people may think different, maybe I will get to that at some point.

And sorry again about the photos, some forums have different standards, now I know what they are here. My apologies for any offense.

 

Well, had a fun experience today. Since I got my silicone chastity device (chinese, BON4 style), I have been wearing it more or less continuously for the last week or so, including at work and in social settings. In general, my perception is pretty positive due to it's inherent comfort. However, a couple of potential issues presented themselves today.

I am currently employed by a large national retailer to unload freight, something that is fairly physical work. At some point during the second half of my six hour shift, I managed to yank myself out of the device and not really notice I had done it until I went to the bathroom at the end of my shift. Honestly, I don't really know how I did it, but it seems that my balls slipped out of the ring when I contorted somehow. Not a big deal, unlocked it and put it back on and I am safely locked back up.

This brings me to my next points; something which I really don't mean to pee in anyone's Cheerios about:

-With chastity devices, security is essentially psychological.

-There is a major balance between security and safety.

Security and anti-pullout features are something frequently bandied about in the BDSM community, but IMHO, it is really more of a means of enhancing the erotic nature of the device. I have read a number of things (one particular quote, describing the CB-3000 as a training device and not a serious chastity device), which strike me as a little odd. If you really want to, you can get out of a device, either by pulling out or physically destroying the device. I have not seen any device, metal or otherwise, that I could not get out of with some tools and about 20 minutes. But that really isn't the point, it is to enhance a fantasy that you are locked up. If you really are trying to escape from a CB6000 on a regular basis, you might want to re-examine why you are wearing it.

Furthermore, I think it is important to acknowledge that with the addition of more security features, the level of personal risk goes up. Indeed, if you lead a more active or blue collar type life, you need to balance the security of a device with the risk of it ripping your genitals off in an accident. Among people just getting into this kink, I think that is really something that needs to be emphasized. Now in my case, it was a positive failure of the device; I wasn't injured and my work was not impeded, the same couldn't be said if there were anti-pullout devices or a different cage design all together.

Again, if you enjoy rube goldberg high security devices or piercings, more power too you. They just aren't something that is ultimately necessary for everyone.

 

Not fell, were pulled out.

 

Well, today was my day to cum. Very weird experience to say the least. It was a long and very horny evening, I was woken up twice by an erection and was generally pretty excited at the prospect of an orgasm. This morning, I unlocked and cleaned up my cock and cage, before then prepping the fleshlight. Once lubed up, I would have two minutes to fuck the fleshlight to orgasm. If I didn't make it in time, it was back in lockup for another month.

Honestly, the main thought running through my mind was that I wasn't going to be able to cum in time. Even though I felt very sensitive while lubing up, I was scared. So, the big moment arrived. I set my phone timer for two minutes, hit start, and started humping away. It felt incredible, but a wave of terror hit when my cock slipped out of the toy, and I honestly thought that it was going to take me a good thirty seconds to get it back in. I got it back together, thrust deeply a few times, and a very intense orgasm hit me. The whole thing only lasted about a minute.

It was an orgasm, so the immediate aftermath was wonderful, even the cleaning up of the mess. Then after a shower, I've been feeling a pretty strong emotional low, like the one minute and the release wasn't worth the effort I put in. I am gonna take a break from lockup for a few days, I kind of feel like I need to see how I feel.

Or jerk off a lot.

 

So I took a break, did some thinking, and settled back into an old pattern. In all honesty, I really missed chastity within about a week, as sex play actually became fairly boring.

I tried to get back into it last week, intending to go back into lockup after a few days of denial. Unfortunately, my will faltered after an orgasm. However, I bucked up and locked myself up 4 days ago, all safe and sound in silicone. Within a day things clicked and I was back in the zone. The feeling of constant horniness is really nice to feel again.

I am intending to go with a looser term in chastity than the last time, with shorter week to two week term with more teasing. I am not being released until late next week, when some new toys arrive. I am building in some defeaters, so I may not get to cum.

I cheated once, after a 12 hour shift on Black Friday. I was worn out, so I took a nice shower and decided to fuck myself with my dildo. I rode it fairly hard and leaked a bit and became really desperate for an orgasm. This is where the CB6000 would have been better, as you can stimulate yourself by squeezing the head of the bon4. In the heat of the moment, it was just enough to get over the edge. It was probably the most ruined orgasm I had. Ugh.

Anyway, I'll stay good for week.

 

Fair enough statement, I am hoping to work up to that. As I stated before, though, I wouldn't find a period of complete chastity (no milking, teasing, anything) to be enjoyable. You don't miss what you can't have. but I would like to try it. The teasing and fighting myself over a release is the thing I find enjoyable, so I like to see how far I can go. If/when I get an actual domme, I would like to engage in that sort of play. I'm gonna try to work more complete denial into my play, setting oneself up for failure can be kind of fun.

I don't necessarily think that there is a differentiation between "real" or "fake" chastity. I got nothing but respect for those who are engaged in it as a lifestyle or are into complete denial, I have no desire to compare what I do to that. At the end of the day, it is wank material for me; it just takes a long time to get to the end result. When I get into relationship, the dynamic will likely change when there is an emotional connection to another person.

 

Billius: I would fully expect that to be the case. And I would be cool with it.

 

Well, the Bon4 type device I have is officially out. Aside from being rather sick of the huge size of the device, I slipped out of the device while working, again.

Once I got home, I resolved to make my CB6000S clone wearable in a rather fanagled way. To fix the irritation issue, I wrapped the ring in duct tape; not a pretty solution, but it will be interesting to see how it holds up. Then, I made a concerted effort at prep work, shaving my balls to and caged region to prevent any irritation. I also decided to go down to the smallest spacer size as well. There was some initial "ball burn", but that seems to have went away. I am on hour three of wearing the CB6000S and I am not experiencing any of the issues I have previously had so far. Regardless, I ordered a old style CB3000 clone with the hinged rings as a contingency in the event this fix doesn't work.
Psychologically, I am back in the state of miserable horniness that I missed so much. Last night was actually rather rough, as I was incredibly horny and the Bon4 allowed a certain degree of erection to occur. I was desperate enough that I tried to reach an orgasm through purely nipple play, though I aborted that effort after about 10 minutes. Switching back to the CB didn't really help much, either. I find the device itself to be really arousing, to the point I can actually start to get hard while looking at it. It weirds me out a bit, and it also makes it something of a pain to stuff myself into, particularly with the smaller spacer size. However, on this particular size, erections are considerably more restrained, though still pleasurable in a nice way. No real stimulation is going to happen accidentally with the CB either, with a vibrator likely being required to orgasm.

I have also decided to avoid cockteasing, as I don't quite believe my willpower is quite to the point where I could resist cheating, as well as a simple desire to experience it. The most I have done was try masturbating though purely nipple play again, buzzing one of them with the bullet vibe from my Rudeboy. Ugh... It is a weird feeling, like the brain is really trying to connect that feeling to the sexual response. It felt really good, but it was incredibly frustrating, as I felt like I could "see" the edge, but couldn't actually reach it. I also barely got hard during it, though it felt like something was definitely going on. About 15 minutes and a lot of precum later, I decided to call it quits.

I have some plans for when I am actually going to have an opportunity to cum. It will take about two weeks for some toys necessary to get here, but I am building in a considerably element of failure to make it more interesting:

Eight Options

1. Fleshlight fuck with cock sheath. Time limit of 1 minute, with a chance to increase if skipped. Orgasm permitted.
   
   
2. Outercourse with fleshlight. Five minutes, orgasm permitted.
   
   
3. Recaged in temp device, 10 minutes of teasing and oral on fleshlight. Uncage. Roll again. If 3 or lower, 5 minutes of blowjob practice with masturbation permitted, no orgasm. If 4, 5 minutes of edging, no orgasm. If 5, 1 minute of stroking with ruined orgasm.
   
   
4. 8 minutes of edging, fleshlight head stim permitted. At last minute, drench cock in icewater, orgasm permission granted.
   
   
5. Dildo fuck to full orgasm. Three weeks of complete chastity.
   
   
6. Delay release 1 day, roll again
   
   
7. Delay release 1 week, roll again
   
   
8. Delay release 2 weeks, no play of any sort permitted.
   

A random number generator will be used for this.

 

I am using the plastic clones, I don't particularly feel like encasing my dick in potmetal. Lol. The duct tape seems to be working, usually the ball burn would become an issue within an hour, it hasn't happened so far. I am excited about the CB3000, as it comes with Points of intrigue. I am thinking about picking up a cheapo curve cage just for kicks. If I decide I really like this, I will probably pony up the money for a HT.