Day 175

I'm so excited for tomorrow, partially because my move will officially be over since I have to return my keys but mostly because I get to see my boyfriend. Oh and have a weekend full of kink of all varieties!

I'm not super in need of relief but a little preemptive play and stress relief will hopefully keep that from happening. While I do kind of like the super intense craving for play it quickly gets to be extremely intense which is not fun. I do like the bit of extra drive and push to make me get out and play, but with weird schedules it's not always easy to make that happen.

But all that aside yay for kinky weekends!!!!

Day 174

I feel myself wanting to apologize for not being interesting lately but I really don't think there's a need. This blog was created to chronicle my year in chastity (and become who knows what after). And in doing so some days will be boring as I've said previously. Sometimes I've found even when my cock is out my sex drive has peaks and valleys. Some times I can't get enough and other days I could care less. Usually this is accompanied by something else happening (like my move and getting settled in). And I seem to be in a valley at the moment.

For those of you wanting the excitement keep coming back this weekend I'll be going to a bondage weekend with some wonderful friends and so new people I have yet to meet. But there is bound (hehe) to be plenty of pictures and lots of stories from the 26 men stuffed in a cabin. ;) So stay tuned and the excitement will flow whether my cum does or not!

Day 173

I'm almost half way there, yay!!! So today was just the usual back to the grind stone after a nice weekend. But it's also Monday so that means picture day.

But as for chastity today it was nothing too exciting but the pains of chastity in summer are coming around. Mostly it's just hot and sweaty, but that makes multiple showers necessary some days which is never fun. It also is interesting in shorts, not that they are much different than pants but it does seem to make a bit of a bigger bulge in shorts. This of course prompts even more people to reach and try to feel my "huge cock". I don't mind but the reactions are always fun.

And my balls hang low which is fun, but it means the device slips an slides around a bit which isn't always the most convenient.

Day 172

This day has been wonderful. I love pride even if my chastity doesn't make an appearance. Lol sometimes it is nice to not think about it too much. My balls have started to become tender from the build up which is fun to an extent because it feels like there is constant pressure on them. Some days though that's distracting and makes it really hard to focus...like today. But I got a nice distraction after work when I went out to pride and even now after I've gotten home and no longer have the distraction just a little bit is all I needed not to notice it for at least the time being.
But it should be interesting soon when the distractions need to be bigger and more intense. ;)

Day 171

Happy Pride everyone!!!! Yes it's that time of year when all the rainbow flags are waving in the streets and naked men dance on floats in a parade. And it's a time to reconnect with where we have come as a community and where we have yet to go. There are many others who have written about this recently so I won't repeat it all. But really the best part of pride is to connect with friends and just let it all hang out, (well you understand) for me. I mean have coworkers telling me they would switch shifts with me because it's my weekend and I should have it off. That's awesome and it makes me really happy to be surrounded by so many wonderful people.

But any ways yay Pride weekend! And my device is still there keeping me nice and tight and locked up. Nothing too exciting happened with it today. I was just reminded why not to wear boxers with it since I've been putting off laundry with my recent move. So yeah boxers and chastity in my opinion suck! So it's a reason to do laundry. Lol

Day 170

Today was moving day which sucks locked up or not so it wasn't too exciting as far as my chastity goes. After it was all finished though I went out to the bars and gt the chance to introduce a few people to the device. That's always a fun and interesting experience but nothing all that exciting.

Day 169

:-)

Yeah I'm really not sure where else to start because I can't stop smiling and feeling wonderful!  I've been getting to know leatherSMPIGboy for a while now.  We chatted before IML and kept missing each other at IML, but finally got a chance to connect today and wow am I glad we did.  When you get two piggy boys in a room together nothing but fun is bound to happen!

This evening he get me securely locked down into his sling to work my ass over hard.  He hooded me, put a collar around my neck to secure it down, put restraints on my hands and then put me in the sling.  Once in, my feet got locked up, my hands were locked under the sling, and secured my head to the sling so I wasn't moving anywhere.  After he got me locked in, he forced a gag in my mouth and attached the blindfold and it was time to go to town.  I sat back just waiting for what was to come relaxing as his fingers start to work my ass open and he worked fingers, hands, and toys in.  But most interesting was a speculum...I've never played with one before and it was an awesome experience! Something very difficult to describe but wonderful.

And of course I had to return the favor and get him all wrapped up in his leather sleep sack, and I had the pleasure of working over his cock.  I tried to keep him on the edge for as long as I could until I couldn't resist making him cum. :)  As a fun little surprise I got to lock him up on orders from his Sir before letting him out of his sleepsack.

Day 168

Play that falls through (especially after talking about it all day and getting me horny) makes me a very unhappy boy!  Typically this makes me very upset because well as I've mentioned before on here playing with myself in many ways is great but there is nothing like playing with another person.  So this disappointment is hard to swallow.  A little more so when in chastity especially when you were supposed to be the top in the play....  I'm not prepared to have fun with myself which kind of sucks more than if I weren't in chastity because I would of have a good night either way with a nice wank. 

Fortunately tomorrow I'm supposed to play with someone else and so as long as that goes as planned I think I can stay a happy boy. :)

Day 167

Another less than exciting day today in chastity.  I'm still locked up and loving every moment.  I'm looking forward to some play that I'm hoping to have soon which will do more than make me a happy boy and keep me content for a while.

But until then more naked packing for me! :)

Day 166

Just another usual day of working and staying busy around the apartment.  Though I am going to be a bit busy for the next week or so.  I'm moving into a new apartment at the end of the week so I've got lots of packing and getting ready to do.  This will definitely be taking my concentration off of my chastity, but I was certainly thinking of it at work today when I was sitting in the office taking a quick break and felt my cock getting hard out of nowhere.  So I decided to capture the moment for my picture today.  Enjoy!

Day 165

Nothing like a cock in your mouth and cum on your face. :)  My and the bf were playing and as usually his cock was fucking my face while I worked over his nipples and balls.  As he was giving my mouth a break and I was jerking him off he came on my face covering it with his hot load.  It was wonderful and I just love playing with cock (especially his).

So it was a good day, but really I've found it easiest and best to simply not think about my cock lately.  And somehow that's still working.  Soon I know that I won't be able to ignore it as it will be getting extremely sensitive and I'll feel it 24/7 but until then I will take advantage of what I've got going for me.

Day 164

It was a good day today, nothing all that special but it was nice. I got the chance to spend some time with my bf and my friends.  Didn't get to have any fun because it was a long day of birthday activities for our friend, but it was definitely a good distraction from the chastity at least.

It was nice not to think much about it but there were definitely times when I was getting hard that I had a really difficult time not thinking about my chastity.  While that is the point of the device sometimes when I'm standing around with friends and can just feel my cock grow in my cage making my bulge just a little bigger; well it can be annoying.  I do have to reiterate, what I told Sir many times during my last lock up but don't think I've mentioned yet this time, I really enjoy getting hard ons in chastity.  While yes it is frustrating not be able to do anything with my cock it's nice to know that it's still working and the sensation of the pressure on my cock is rather nice.

Cumming would be so fantastic, but I'm certainly ready to wait for Sir to tell me when that will happen again.  I'm not sure what was different after IML and after this last lock up after playing with Sir, but I'm in a much better position to last the long haul.

Dat 163

Ahhhh, I still feel wonderful from yesterday. But still horny.

Really a pretty good day though in general because I was super busy the whole day and work was just intense so my cock is the furthest thing from my mind. Though it's interesting because most days had that happened I would have totally been all about my cock. I would have immediately gone home and jerked off. Today I haven't been because it's not an option and I've just learned that. It doesn't bother me and part of me thinks that's because I know my cock won't really help the issues.

Though it feels wonderful I've also learned there are other ways to feel good after a long day. So it works out well for me, but some days the quick relief would be wonderful! ;)

Day 162

I was horny so my ass paid the price, and I mean that in the absolutely best way ever!  While it may be a sloppy mess right now I don't think it's ever felt better.  And well I could barely care about my cock right now it feels that amazing.  I'm really glad I'm a bottom otherwise I think long tern chastity would be completely impossible.  If I didn't have that to take my mind off of it I probably would have lost my mind by now.  But since I can sit back and open it up with my toys it gives me a moment to just forget about my cock entirely and focus on bringing myself great pleasure through my ass.

I only captured a few pictures this evening but I do have some video of he fun below the pictures after the jump.  

Unfortunately I don't have the wonderful video of my fist going in and out of my ass but if you have any serious doubts about that you can ask my bf since he was watching the whole thing live. :)

Day 161

The horniness is creeping back bit by bit, but still very tolerable.  Though I'm starting to crave a serious session with my ass, I haven't had one in a while and I'm hoping I can find someone to open it wide soon.  I'm a pretty big bottom before I'm locked up and it just gets worse when I am.  Like the other night when I was playing with my ass for almost an hour.  I would never do that by myself unlocked.  After the plug went in I would have been jerking off and done in 20-30 minutes.  But all locked up I ride that plug, pull out a dildo, lube up my hand and work it over until it's nice and stretched out.

Honestly while I lay in bed thinking of the perfect scene (or at least in my fantasies) right now it would go a little something like this...

My eyes blink open just waking up from a good nights sleep and as I try to roll over to give my boyfriend a good morning kiss I can't move.  I try rolling to my right and I feel my ankle and wrist tug against a restraint, and as I try my left I feel the same thing.  What the hell, I think to my self as I hear the showering running in the other room wondering what he could possibly have planned for me I know he has to work today.  I always knew him waking up so early was going to get me in to trouble some day. 

As I lay there helpless to get up the shower stops and I hear him walking this way. "Oh you're finally awake, I was wondering when you were gonna get up I thought the restraints might do it, but apparently you really do sleep like a log."  

"What's going on babe?  I though you had to wo...." I try to finish as he slides a gag into my mouth.  

"That's plenty of talking for you, just relax and enjoy your day off.  Trust me you're all booked up with plenty of things to do today."  

I still don't know what he's talking about I had no plans today but doing things around the apartment.  

He unhooks my legs from the ropes at the foot of the bed and links them to my wrists putting my ass straight up in the air takes off his towel to show my his hard on, grabs a condom and some lube and starts pounding away on my ass.  He just keeps going enjoying every moment making me moan and groan with pleasure as he hits my prostate milking me as my ass tries to drain his cock.  

As he keeps going I can tell he's getting close but I don't want it to stop and I groan a little almost whining a little so maybe he'll get that I want more.  But he keeps going hard and fast until he finishes in my ass pulling out his cock as I moan and give him a look saying I'm not finished. 

"Oh I'm just the first in a line for you today boy," apparently he had gotten what I was trying to say but there were other plans for me.  As he lets my legs down and reattaches them to the ropes at the foot of the bed he says, "Some friends might stop by later, don't go anywhere and play nice."  

"Yesh Shir," I mumble through my gag.  While I know that he would only let people he knows in, who could have all lined up for me it's a Tuesday, people have to work!

He finishes getting ready gives me a kiss on the gag, "Have a great day boy, I'll see you when I get home."

Day 160

So today was another day without much notice of my chastity.  Like I've said before it comes and it goes obviously I just got over an intense time with it and have the chance to relax for a bit.  It's nice not to have my chastity on my mind 24/7 which is really what it feels like when I get to the point of the intense need to get off.  I notice the device certainly to the point that I know it's there, but my cock isn't feeling it yet.  And yes there is a difference.  I  can feel the device there around my cock and on my skin etc, but it's just there and of course I can feel it on my cock as it touches it.  Though it's a different feeling when my cock has become sensitive enough that the smallest shift in my device starts to get me hard and drive me wild.  There are many different sensations that go on in chastity and they come and go with the feelings that I have.

Day 159

Ahhhh, still feeling wonderful after yesterday!  So nothing too exciting for me in chastity but today is Monday so it's picture day, enjoy! ;)

It's a simple picture from a simple day...

Day 158

Sir is amazing and while I hate the secrets he keeps while he keeps them they are always well worth the anxiety. We had planned to play with one of his friends which I was very excited about but he told me I wasn't going to get fucked. And well I was a little miffed (okay pissed). I said yes Sir and went with it, he always comes up with something good for me.

I was still a little put off this morning when I was thinking about it because I had no idea what was in store for me. I went through my day a little anxious but trying to keep calm about it. For some reason I the intense irritation hit very quickly after getting locked up after IML so keeping calm was a challenge. As time rolled around and I was driving up I was exhausted from working and needed to have a good time.

I met Sir's friend. Very wonderful man and went down to the playroom and got ready to get tied up still a little nervous about it. But as I got tied up to the St.Andrew's cross and Sir got tied up next to me, he blindfolds went on and the flogger came out. I was starting to get very excited and the flogging commenced alternating between the two of us pounding the moans out of us. It was wonderful, though I like it a little harder, but as a first meeting it was fantastic.

After my back had been turned red and was nice and sore I was let down, tied and and bound to a table. As I was starting to wonder where this was going I felt and heard Sir get bent over the end of the table and I knew why that was happening. He's gonna get fucked but before he got tied down a dildo was put up my ass and tied in place. (That was nice but it's certainly not getting fucked...)

Sir got tied down and his friend starting playing with us wrenching on my nipples and then hitting them with a crop making me moan and groan. And Sir was burying his head in my crotch licking my balls and such. Then as time goes by I hear noises coming from Sir. He's about to get fucked! I'm slightly jealous but then I feel some hands on my and the crop back on my nipples. Plus with the whole table moving and so the dildo in my ass was feeling good.

Then I feel my device getting pulled off and I had no idea what was happening until it was off. My cock was exposed and Sir's mouth was slobbering all over it and I was so close I could barely hold back. I was cumming and he just kept going until his friend was finished with his ass driving me wild. As we were all moaning in pleasure.

All of the awesome rope work and good times provided by Chicagoasiantop.

So yeah I have another day of chastity but it was worth it to get out of this crazy mood. Though some would say it's not really chastity if I get out occasionally but that's our arrangement so I do as Sir says and if he wants to get me out and play with his cock he's more than welcome. ;)

Day 157

Not too bad today just super horny again, bud definitely wanting to jerk off today....and bad!  Nothing simple is taking off the edge which is slightly obnoxious because I could really use a little less intensity.  I am supposed to playing with Sir and someone else tomorrow which I really hope helps this situation.  Really I don't know what I'll do if it doesn't because I've gotten really horny and my anxiety has built up really quickly since getting locked back up and I can barely stand it.  This doesn't bode too well for the rest of this year, let's hope it's not something that's going to stick around.  *crosses fingers*

Day 156

My fuse is getting short and I'm not sure why. Okay well maybe I know a little, I wanna get off! But typically this isn't what happens. I may get a little grouchy some days but I don't want to punch walls. Of course part of that is work which has been super draining and difficult the past few days but typically I'm good about dealing with stress etc. I think there are probably a few other personal contributions going into the pile this time. In reality though I'm thinking about it and while it would be nice to jerk off that would do absolutely nothing to help me through these situations. Yes I would briefly feel better and get the endorphin rush of it all but talking it out with friends and loved ones gives me better perspective and ideas for actual solutions. Which is probably the better approach, but getting off definitely is in need sometime soon, not necessarily even cumming in chastity but a real good scene would set me right!

Any volunteers? ;)

Day 155

Today has just another day horny as can be just doing what I do.  I'm in the process of looking for a new apartment and kind of in a crunch time so that takes my mind away from chastity quite a bit, but it's definitely always in the back of my mind at the least.  I will be completely honest when I say I do try to keep myself busy doing a variety of things when I'm locked up because it does make it easier.  The worst days are the lazy weekends when I don't have much going on...luckily there aren't many of those happening.

Day 154

So I might just be over thinking this or just searching for something profound to make this experience even more worth while. But I think one of the many things you are denied in chastity is intimacy with yourself. I know that sounds a bit odd and maybe it is, but I've thought about it recently that one of the quick easy and thorough ways to be intimate with ourselves and fulfill that need is through masturbation. By bringing myself to that level of pleasure I have created a simple sexually intimate moment with myself.

I think that is what I struggle with the most in chastity is filling the holes that jerking off used to fill for me, one of those being those intimate moments of jerking off.

I think it can be had through playing with yourself in other ways, but it's definitely a little bit harder.  I mean getting my hand up my ass takes a little longer and more effort than even edging for an hour.  But it results in the same feeling of bliss and intimacy with myself.  It's much easier with someone else and being able to have that connection and intimacy that comes with that fun and bliss.

Maybe intimacy isn't the right word to describe the connection and the experience that I'm trying to describe but it's what I got.  

Day 153 - Update

No plug all night, instead my hand was halfway up my ass for almost an hour and then up there for a little bit. ;)  Yeah I'm a really happy boy, but no cum for me tonight as it should be. :)

Day 153

It's a horny kind of night!  I was really pretty calm all day and then when I got home (after installing the air conditioner because it was crazy hot today) I got all kinds of horny.  I decided I hadn't really spent much time in the rubber that I purchased at IML and so decided it was time to pull it out (and with the A/C in I didn't think it would be a problem).  

So I pulled it all out, my new jock, shorts, and sleeveless shirt all from Fort Troff an awesome store with a huge variety of stuff from gear to toys.  I lubed it all up and threw it all on and of course snapped a few pictures.  But before it all went on I had to plug up, so I pulled out my favorite plug and popped it in my ass filling me up, just enough to make me a happy boy.  

As I was taking the pictures I kept going in and out of my room and with the rest of my apartment still A/Cless I was dripping with sweat after the third picture.  I was totally loving it though!  It's taken me a little while but I'm really coming around to rubber.  (Though leather will always be my number one choice for gear.) So after a few snapshots I lazed around in my rubber which was a great feeling just covered in the tight feeling of the rubber hugging my body.  After a while though running around my place I couldn't get all the way cooled down so the rubber had to come off, but it was nice to get a little fun out of it.  My plug is still in and after I play with my ass for a bit I plan to stay this way all night.  I'll let you know how it goes tomorrow, but it's certainly not my first time plugged up for the night so I'm pretty sure I'll manage. ;)

Oh and here are the photos...

Day 152

SSDD, nothing too exciting today and with lots to keep me busy not much time to think about my cock thankfully. My cock and cock in general on my brain lately has been taking a bit out of me to be honest. I mean as you know, I love it, but it's a lot to constantly be horny and wanting it. When it's the thing trying to dominate your brain while you're trying to be productive and do chores or get work accomplished.

So another good cockless day for this boy, there will probably be more of those than cock filled days. But those are the ones I look forward to.

Update: Yeah I screwed up again and forgot a Monday picture. But here are a couple of one of my favorite purchases from IML, a pair of bleachers. I for some reason have been really turned on by the skin look lately (though certainly not the haircut). And the bonus I didn't know until I was in line to but there was a zipper in the back. :)

Day 151

I want cock now! Not necessarily my own, but that's how I've been feeling all day.  I just want to play with one.  They are just wonderful and it's one of the things I miss so much about chastity.  When I can't find another cock to play with I had my own, like a default.  

Again though it's really nice to not have one all the time.  Honestly if I lived with my boyfriend and my cock was locked up I would be over it all the time, kind of like when he comes to visit. :)  It would make the experience a little easier, but I think it would also lessen the experience a little bit (yeah I like to make myself suffer a little bit).  I think it makes it fun for the other guy to because I'm so cock focused that I will suck it until my jaw locks up or have them pound my ass until they want to be done just as long as I get some cock in my life. 

Day 150

It's always interesting who will and won't be thrown off by chastity. I was out with some friends last night and just enjoying a good evening and then a friend of my friend started getting a little frisky with me. I wasn't complaining but of course as I always try to provide full disclosure if it even feels like things are going in that direction so it doesn't become a problem. But he just brushed it off and said it was kind of hot. That was not the response I had expected. Nothing ended up happening past some making out but it sure was a pleasant surprise coming from a person who didn't really seem to be all that kinky.

But enough about yesterday today I finally unpacked from IML and had so many memories flooding back which was great. Of course remembering having my cock back was just a horrible tease but I guess I should have expected that really.

Only a couple times today did I crave it back, hopefully they start going away. If I keep craving it like this it's gonna be rough.

Day 149

Today I'm going to be a good boy and post before I go out, my punishments are piling up.

Today wasn't too bad but it's definitely been a little rough going back in after so much freedom. I know I've flip flopped a couple of times on it but I had a moment where I really wanted to rip off the device and jack off. I looked at my cock and almost out loud said "I miss you.". Luckily I was alone for this precious moment and didn't actually say it just thought it. I have a difficult rest of the year ahead of me but I'm looking forward to it. The desire to have my cock back will wax and wane and I just have to make it over this hill.

Day 148

Well I can certainly say chastity doesn't impede my going out and having a good time. Though going out can make bad things happen like today with my post coming long after it was due. I will certainly have a punishment coming for this but what I have no idea. That's kind of what Sir enjoys most. I will dread the punishment for a while. And of course it's never as bad as the horrible ideas that I come up with thank goodness. I'm sure there will either be photos of it or a story for me to tell on another day.

As for the chastity meh, I barely notice it again. It's just a part of me.

Day 147

It's was quite nice having my little reprieve and it's actually made going back in slightly more tolerable.  I no longer feel like I'm riding the edge of cumming 24/7 which is nice for a change.  While it was enjoyable it was also very intense.  And it meant I was cumming every time someone touched me. (Not that I'm complaining about cumming!)  I doubt it will take long for me to get back to the point of being on the edge, but until then I'll enjoy my little break.

It's odd that even though yesterday I was reaching for my cock from time to time I haven't done it at all today.  Apparently it didn't take long for me to get back to my locked habits.  Fortunately I got a decent fill in my ass while I was at IML.  But it will be craving something soon I'm quite sure.  Got to keep myself a happy boy.