The new blog!

I've started the new blog!!!  It will be rather different than this one chronicling the last year I had in chastity, but I'm excited about it and I hope that you will find it interesting as well.  I hope to do lots of fun things with, namely writing the tales of my growth as a kinkster and the kinky community that we all live in.  While that may not be the most interesting thing at times I find it interesting so you'll have to deal with it.
Don't worry I'll have plenty of other fun and interesting things to go along with those posts about my exploits and fun.  So go check it out!

The Ramblings of a New Old boy

Freedom Day 9

Today was busy but it was nice and I didn't get off!
Yes yes how can I not get off my cock is free and I must want to so bad, but really it's not like that. Yes I would love to get off 24/7 but really it's not necessary and I realize that. Of course sometimes the urges are intense and other days they aren't but never are they so much that I have to stop everything I'm doing and jack off. Actually it's never really to the point that I even really have a huge desire to get off. I just think to to myself oh that would be nice I have the time for a little fun I might as well do it.

It seems so weird to before I went into my year, I had a routine and a bit of a ritual each day, but now it's just when it seems like fun. Even then it's not a big deal, having an orgasm on my own is nice yes...but it's not awesome. That happens when I have some leather, bondage, or a great time. :)

Freedom Day 8

Today was nice and I love starting off the day with a nice edging session.  Granted it was only about an hour but it was so nice to wake up and grab my morning wood and enjoy myself.  It's been so long since I got the chance to do something like that.

For all of you who have followed this blog I will be continuing another blog soon, but I don't know what I'm going to call it yet or exactly what's going to be on it.  Of course it will be kinky and I'll talk about my exploits and adventures, but I'll see what form it takes as I begin it.

Hopefully I'll come up with something clever and start it in the next couple of days, but I will keep you posted as soon as it happens.

Freedom Day 7

Ahhh what a wonderful weekend, but it did have to end sometime.  As I come back to normalcy and my day to day life I'm very glad to have the opportunity to do the things like MAL.  I love being in the company of people that understand my fetishes and kinks.  There is something very freeing and liberating about being around that group of people, even if there isn't a discussion of fetish etc it's good to know it doesn't matter.

But really this doesn't just have to happen at these major events.  Many people have recently spoken about BLUF's 12x12 Pledge to go to the leather bars in gear 12 times of the next year. These are the places that we should be enjoying ourselves as well and letting all of our flags fly!

As for my chastity, this blog will probably be coming to a close in a few days as that adventure has come to an end.  It has been a wonderful year and I have learned plenty about myself.  I have noticed though I do enjoy jacking off again (A LOT!), I don't really feel like I need to though.  I'm not sure exactly how I feel about it but it's interesting.  It definitely gives me a different perspective on sex and such.  There are some people who do long term chastity for this very purpose, but that was not my intention.  It just kind of happened, but I'm still plenty horny!

Freedom Day 6

Yet another awesome day at MAL! It's a spectacular event that I can't wait to come back to!

Aside form the being out of chastity, getting to play with my boyfriend and getting off in a variety of awesome and fun ways there was so much other fun stuff happening. I met awesome people, and got to see others I haven't seen in a while.

But today was awesome I got to try out my boyfriend's new padded hood and his neoprene sleepsack. It was a great time and I made a big mess enjoying being able to get off from my cock.

I'm really looking forward to a nice long edging at home by myself though. That is one of the biggest things I've missed being locked up.

Freedom Day 5

Today was wonderful, I got caned and got to cane a friend. It's always an enjoyable experience, but it was fun practicing on someone because I've never done that before.

I also got to have a lot of fun with my boyfriend which is always wonderful! He sucked me so much I almost exploded so many times. I finally got off and he shot all over me and I couldn't have asked for much better.

Freedom day 4

First day of MAL and it's wonderful! Great people, great conversations, and hot men everywhere!

I'm really glad that I came out here for this weekend for many reasons but it's already been great, and I've cum twice since I last posted. Once was last night as I was going to bed me and my friend got a little frisky and he gave me an amazing blow job.
Then today I met someone online here at the hotel and and he just happened to be free tonight and so he came up to my room and had a wild time until I couldn't resist cumming and then we continued our wild time until he had his fill.

Both were wonderful orgasms even this far from getting released they feel absolutely spectacular and so much better than I remember.

And yes today's post is late, but it's hard for me to remember to post or even post by midnight when my evenings have only just begun at midnight. But that is no excuse and I'm sure Sir will find some way to deal with it.

Freedom Day 3

I flew out for MAL today and took myself out of chastity for the plane ride. I just wanted to go through security without chastity for once! It was very nice and a much less anxiety inducing.

But as I was reminded yesterday that I didn't finish the last two months of chastity. For those two months i was doing well but really horny! I also had a fun time working up a jock for a friend of mine filling it with my precum and working my ass daily. I also filled it with a little cum after pounding my ass to drain it.

After that Sir made me play with my ass weekly which was really nice even though sometimes it was tough fitting it in. I always enjoyed it though!

And as you probably know it ended with daily spankings which were difficult but really good because I did deserve them and I got to see Sir every day which was really wonderful!

Freedom Day 2

I had a lot of fun last night...with my sounds! I haven't really been able to use them for a while so I decided it was definitely time to have some fun with them. I especially wanted the metal sounds, but I have to say the silicone one felt completely different unlocked. I could feel the ridges while I jerked off with it down my cock.

But also I'm locked back up again because I don't want to just be jerking off 24/7 until MAL which will e even more fun horny so I'm locked up but holding my own key. :)

Freedom!!!!!!

Today was the day it all came off, my year is complete and it was amazing!!!

It was a day earlier than Sir and I were planning but because of schedule issues it was today or after MAL and neither one of us wanted that!  So we did it today and I'm sure down the line he will do something to make me pay for getting out today.

As soon as it came off he immediately started to suck my cock, and he didn't stop until I was cumming and shuddering with pleasure!  After that I tied him up to have more fun and got to return some of the spankings he gave me and spanked his ass.  It was a lot of fun and I got him nice and red...for what I can do.  After I was done with that I flipped him over and took off his chastity and got to suck on his cock and then decided to hop on and ride his cock.  It'd been a long time!

Once I'd had my fill I got off and made him cum and then came again all over him which felt amazing again!!

I loved my chastity experience this past year, but I will say I don't think I want to go that long without touching my cock again.

Day 370

Today's spanking was very interesting, intense and hard for one. For two Sir rotated between his two canes and one of his wooden paddles. It was far more intense than I expected (don't know why just was).

Months 9 & 10 were interesting for me as I was starting my grad program. I was anticipating it being difficult and really pressuring me. It wasn't too terrible, but it did make for some difficult study nights. But in other ways it helped keep me focused and from not masturbating excessively when coursework got stressful.

Day 369

Um....wow! But I'l get back to that. 

Today was a  good day nothing too exciting but Sir used the wooden paddle on my ass which again was a nice.  It was also my last day of mandated playing with my hole.  While that was a little sad it was also nice because mandated playing with my ass was odd.  Whether I wanted to or not I had to do it which was good, but again a little weird.  

But before I got to playing with my ass, I had finished cleaning out and got a message from someone I'd chatted with on asspig.com.  He was looking for someone to fist tonight and I was already cleaned out and ready to go.  Since I was ready to go and already had to play with my ass I was absolutely ready to get fisted.  I went over and had one of the most intense fistings I've ever had.  I have been fisted a few times before but he started out by putting a speculum in me and fucking me through my open hole loosening up my hole.  Then he took it out fisted me and then soon started punching my hole opening it wide and stretching it.  Getting my ass punched was awesome!  I really can't wait to have it happen again.  

But of course I had to do my hour on my own as well when I got home.  It was very interesting playing in my whole which had already been sufficiently wrecked.  

As for the months 7 & 8 they were both very nice.  In August I got to spend two weeks with my boyfriend where I got a little surprise and was allowed to get out a number of times without repercussions.  This was a little shocking for me but it was amazing and greatly appreciated.  I'm pretty sure it helped keep my crazy at bay. 

Day 368

Today was a little interesting. I was out with some of my friends and we were going to continue our evening so I told them I had to stop by Sir's house before going out because I needed my spanking for the evening. So we got to Sir's place and they decided they wanted to come in and watch. I wasn't going to complain it wasn't really going to make any difference.

He hit me while they watched and I think cringed a little but it's what I do so they weren't too surprised.

As far as my reflection on the past year today is months 7 & 8. I those were another couple of fun months as in August I got a surprise when I went to go visits boyfriend but around this time it was a little difficult because Sir and I were both very busy and not finding time together so I was struggling but making it through. It wasn't bad just weird because I was accustomed to talking to Sir and seeing him at least regularly if not frequently. But Sir was wonderful to me by letting me out with my boyfriend when I went to visit him! Which was a surprise but a wonderful one!

Day 367

Sir was very kind to me today and only used his hand on my ass.  I felt like a very lucky boy not getting a cane or paddle of any sort today, but I do have to say it was a little weird, good weird.

Months 5 and 6  were a really good build up.  It was good build up for me because I knew I was getting out for a bit during IML which was a wonderful mid-year reprieve.  But it was also wonderful because I got my new silicone sound which was amazing for the time that I was locked up, until Sir forbid me to cum while using it.  Then it was a little sad having such a fun toy and not being able to use it.

But after getting out during IML it was frustrating but also very nice to get locked back up knowing that I was about halfway through my year.  I will also say I think this may have been the time that I begin to play a little bit less.  I feel like at some point I begin to just be less horny (or at least able to ignore my horniness better).

Day 366

I had a good day today just relaxing, until I met up with Sir.  He was playing with another someone and he wanted to spank me in front of him which of course I also though would be fun.  It was a good time but it was another intense day with 18 hits.  Six from a wooden paddle and then 12 from a cane.  I won't say it's the worst I've ever gotten, but Sir is definitely working on a bruise that I've got going on my ass.  It keeps getting more and more sore, but it's bearable yet incredibly intense.

Continuing my reflection on my past year in my 3rd and 4th month I have to say I was pretty busy!  I was very adamant about play with myself and others to keep me from getting too frustrated.  I have to say it was a really good time for me.  I also got off with Sir because I had gotten a little frustrated.  I also started having we dreams around this time which were awesome and super intense!  So it was a great couple months in chastity, but the way that I handled it was much much different than how I'm handling it now.

Day 365

Okay tomorrow I'm really in for it. Another late post and Sir and I didn't get together today because of conflicting schedules. I deserve it but boy am I not looking forward to it!

As for my retrospective, the first couple months of my chastity were not too bad.  To start off I was out very soon after getting in when I went to go visit my boyfriend.  I was taken out of Sir's chastity and put into his.  This caused me a few extra days but they were well worth it.  Of course this really just made it feel as if I was starting all over again after I left him, but I can handle the beginning of chastity fairly well. Some people become antsy and miss jerking off immensely.  Personally I don't feel the desire to jerk off constantly.  I do enjoy watching porn frequently which may cause a greater desire to jerk off, but since I don't have the option to masturbate it really wasn't too big of a challenge.  In addition I had been locked up for 3 months and made it through those successfully so I wasn't too worried that the first few month would be a huge challenge.

Day 364

So this morning when I got out of the shower I did my usual ass check to see what last nights beating left behind. This morning after an intense night that left an immediate bruise there was nothing! I could feel it was a little sore but nothing visible, and even I was a little shocked.

Tonight though when Sir saw my markless ass he decided he just needed to hit harder and that he did. There was no bruise yet when I left, but if there's no mark tomorrow I'll be surprised.

On a different note though I will answer a question I got recently in person and on here.

Frequently when people find out that my boyfriend is not my Sir they are initially a little shocked and then rather inquisitive. I don't mind answer how the complex situation works, because it works. I have a boyfriend whom I cherish dearly and then I have I Sir who is very important to me and I respect greatly. Sir and I met before me and my boyfriend, so he met me collared and knew that having me as his boyfriend meant that I would still have my Sir. This was discussed a few times and because we both already knew we wanted an open relationship it was not a giant leap for us. Also I told Sir all about my boyfriend and they started chatting soon after my boyfriend and I became official of not before. And they talk to each other frequently sometimes to my detriment but it's usually good for me.

In that manner they collaborate on things and I talk to both of them about the things that we do. It's also god for me to mention that my boyfriend knows I really enjoy the things that me and Sir do so he is comfortable with it because he knows that I'm having fun and enjoying myself. That allows him to be comfortable with it.

So yes sometimes there are difficulties but we talk with each other and we make it work because I think there is something we all like about the situation.

Also soon I will be starting a little retrospective about my year reflecting on highlights and lowlights tomorrow.

Day 363

So after this weekend which was amazing I went to go see Sir. I knew I was going to get my six spankings for today and some sort of punishment for being late on a post the other day. Of course I knew it wasn't going to be good but I did not know I would have to make up the day and then have another 6 for my punishment.

So today I had 18 thwacks with the cane....it was an intense time. I kind of knew it wasn't going to be great when I was strapped down, but I was not expecting 18.

Day 362

Oh Sunday funday, it's wonderful! While this weekend has been absolutely fantastic, getting to play in my ass for an hour was very nice! The rest of the group was out playing a game Sony grabbed my lube and dildos and had some fun.

While it was a bot odd playing by myself with so many men around my ass felt so good! I set a timer and didn't stop until it went off. But I also tried a new lube that I used while fisting but really got to try it put today. It's a power lube made by sledgehammer and it was amazing!!! I have decided I love powder lube it's just so slick and awesome.