Challenges

This was an evening where Hawk basically said, let’s go for a walk and get you naked. A lot happened that night, and it was a really hot time all around, but I’m going to stick mostly to letting the photos speak for themselves.

I started in only a pair of short shorts (commando) and a tank. Right away, Hawk pulled the tank off—he didn’t ask, he just said it was coming off. For the rest of the night this is all I had on:

Nothing but short shorts

This is all I was allowed to wear the entire time

I wasn’t with Hawk for 5 minutes before he said, “hey, what’s that brightly lit area over there?”

Good lighting basically meant it was the first place I was going to get naked that night.

Statuesque

Just needed to toss my shorts off to one side

This was on a bit of a side street but still easily visible from the main strip. As I stood there I was watching the pedestrians go by hoping none of them would look this way since I was completely out in the open here. I didn’t stay naked long—you can see I didn’t even take my shorts off all the way—but it felt like ages. I started getting the feeling it was time to move on, and we kept walking. (Hawk was actually nice enough to give me my tank back to help calm my nerves since I was feeling particularly exposed after that, but he stripped it off again after just a couple blocks.)

We later were able to find a couple alleyways that were nicely off the beaten track, and this time Hawk made sure it all came off.

Everything off

Everything off

Exploring a bit more, we came across a particularly secluded alley, long and twisty with a dead end. I got really turned on here, feeling a bit safer. My clothes were dropped in one corner and we walked around a bit, me fully naked now, still visible from the streets in some places. I was so turned on by this I really felt like I needed to be used and taken advantage of.

Begging to be used

Begging to be used

I did get a bit of action in that alleyway but not nearly as much as I needed. That was the end of the outdoor photos, though. I didn’t get to cum, but we definitely did continue the adventure behind closed doors for a bit. I’m going to leave the rest to the imagination for now though.

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I woke up hard and horny this morning as usual. 18 days since I last came. It was about 6am when I woke up, and even though I could be sleeping in on this Saturday morning, my hard on wasn’t having it. It needed attention.

As is my usual routine I went online, I got into a really fucking hot conversation with a really hot guy on dudesnude, talking about getting naked in public. If half the stuff this guy said he’s done is true, he’s got balls.

He wanted to meet up with me and make me strip for him.

Then let’s go for a walk… I will say strip now! And no matter who can see you you have to take your shorts off, then shirt. You will not have underwear or shoes. Flip flops only. You will walk while stripping and hand them to me. I will decide when and where you are not naked.

I was rock hard and he knew it, but he wanted proof that I was actually going to be willing to do what he said when he said it.

I need you to do a dare for me today to prove your obedience. I want your to take a fully nude fully erect selfie anywhere outdoors and public. No private patio or enclosed backyard… that’s cheating.

You will send your pic to me via SMS text by no later then 7pm.

Normally when guys order me to take pics for them it doesn’t work for me; I really have to be in the mood for it, and I have to be into the particular pic he wants. This time, both were right on the money. I knew if I was going to take a pic like that I wouldn’t be able to do it later in the day. It was 6:30 am now; this is as quiet outside as it’s going to get.

I already had a place in mind. I put on a plain white T-shirt, thin gym shorts (no underwear), and flip flops, and was out the door with keys in one hand and phone in the other.

Once outside I walk for a bit until I find the secluded corner I had in mind to try this. I was pretty sure I couldn’t be seen from anywhere, and nobody was around on the street. My shirt came off and I threw it down onto the pavement as I approached where I knew my shorts would be coming off. Already I’m turned on just being out in public without a shirt. I get my camera app ready and start thinking about how I’m going to do this. Starting to watch for people, thinking how quickly I can get my shorts off, where I’ll throw them to be out of the shot but still handy to get back on quickly if I need…. then I remember I’m also supposed to be hard for this pic.

Ok, I thought, getting hard isn’t going to be a problem after 18 days, but I want to be ready when the shorts come off. So still with shorts on, I start jerking off through the material.

Fuck, I realize, this is actually going to be dangerous. I can feel myself getting close to cum and I’m not even hard yet.

Stop. Take a breath.

Ok, off the edge a bit, keep going, going to get rock solid for this pic, out naked in public….

Getting harder, getting closer again…

Fuck, too far, wait, stop, gotta relax….

FUCK! Too late, before I can even loosen my grip I realize I’m cumming already, right there in my shorts.

Fuck, my shorts! This is all I have to wear and after just two spurts it is already starting to soak through, dripping down the outside.

Without even thinking if the coast is clear, and still more out in the open than I was planning, I shuck the shorts down to my ankles and try to aim my still-cumming cock further out so it lands on the pavement instead of in my shorts. After 18 days there’s a huge load and all of it is coming out.

After I stop cumming I’m just in a daze for a second. Ok, gotta get a pic to prove that I was out here for that guy. So I snap a quick shot (it wasn’t a great one so it isn’t going online here, sorry) and pull up my shorts again. They are soaked. There’s a huge cum stain in the crotch and down one leg. And there’s nothing to do about it.

I start walking back along the sidewalk, pick up my t-shirt and put it back on on the way, hoping every hope I could that I wouldn’t pass anybody getting back into my building. Happily, I got lucky on that count and did manage to make it back to my apartment without being seen.

I sent the guy the pic I took, and I think he was overall satisfied though he did say he’d have to issue another, harder challenge for not being hard in it.

After that, of course, I lost a bit of my nerve and we never did follow through with meeting him. We are still in contact though so it may yet happen. Who knows what he’ll make me do in person… especially if he catches me after a few weeks again.

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Sucking cock

Happily the light was much better for this photo.

I don’t know whether it was because I was still on a high from swallowing that guy’s load yesterday, a rush of endorphins from the start of the long weekend, or both, but tonight I felt like I was in overdrive. I don’t think I’ll go into too many details this time, but suffice to say that by about 9 pm I had sucked off a hot thick latino guy in a park by my place despite the freezing temperatures (I tried to take a pic but there was not enough light), and by 11 pm I had a new video to post on xtube.

Thinking back on it I wonder if I was giving in a bit too much, and even now maybe admitting a bit too much by putting it on the record here, but having still not cum in weeks it just felt right. That’s a theme that continued a bit later when I started texting with Hawk, and he started saying things like this:

I think about forcing a collar on you all the time.

I want you to resign yourself to wearing a collar everywhere.

Last time he had locked the collar on me, we had negotiated that I would only wear it for a week, using the excuse that I had a date with a guy the next weekend and didn’t want to scare him off. When he unlocked it a week later, he told me to take the collar and the lock home, but kept the key for himself. I think he like the thought that if I caved and locked it back on, I wouldn’t have any escape without his permission. With that context, he sent this:

I feel like it’s time to lock it on you and keep it on, and if you want to talk logistics and fears we do that while it’s locked on you.

Throughout our whole conversation I was incredibly turned on, knowing he was right, knowing I wanted to feel the collar locked on and feel the significance of being his pup without any negotiations about end dates or when I might need the collar off for whatever lame excuse my nerves might want to come up with. Immediately after that last text, he said:

We can continue this tomorrow, I think it’s time for bed.

But I had to text back

Too late.

and told him to check twitter, where I had posted the evidence of what I had done by way of my first Vine. Turn on the audio and listen to that click.

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My encounter tonight in the sauna made me realize something, which I had actually alluded to in a previous post as well. Part of the reason for this experiment with not cumming is to feel what it’s like to stay horny, on this hormone high, and let that help me embrace my kinky and sexual side (as well as making it easier to integrate that into the rest of my life in a more well-rounded way).

Unfortunately, I find now that not being able to cum is also restricting my sex life in unintended ways. Recently with the cute guy offering me a blowjob at the gym, being so close to the edge meant I couldn’t make the most of it. Sure, I could have blown him, and certainly part of the intent of this challenge was to make me more unabashedly slutty and submissive like that, but 1. that wasn’t the situation that presented itself and 2. when I get this horny it’s pretty easy to get me into a top mood.

So, this makes me think that the challenge as it currently set up isn’t aligned properly with its goals. And that makes me think a rule change might be in order, although, to be clear, I’m not changing the rules yet, I’m just soliciting feedback for now, and will discuss it with Hawk. Some elements of a modified challenge might be:

  • Cumming by someone else’s mouth or ass could be allowed
  • As above, but only a limited number of times, say, once a week tops
  • and possibly also only if I cum without touching myself at all
  • which might allow for other guys to jerk me off or fuck the cum out of me…
  • Then the challenge might be modified to be only 12 times jerking off alone
  • or only jerking off once if I haven’t otherwise cum in the last month
  • or some other variation

Personally, I like the idea of being allowed to cum if I’m with another guy and if it’s without touching myself, and otherwise only being allowed to jerk off if I haven’t cum for the previous month.

This would kill the “12 shot challenge” moniker, since I could well cum more often than that, but it would reduce the effect of limiting my sexual activity while still making sure I stay horny otherwise. It would create an incentive to seek out sex more often, which could either be a good or bad thing. Bad if I abuse the privilege and seek out encounters whenever I feel like jerking off, but good if it means I’m more able to act on those urges building up and riding those highs (in a healthy way). To be honest, I think I would still tend towards not cumming, especially in sexual encounters where I was in a sub/bottom role, because I know how good it feels to keep the anticipation running high.

Oh, and perhaps I should also mention in the interest of full disclosure that there is a really hot guy who has explicitly told me he wants to fuck the cum out of me sometime this week and I don’t want to leave him disappointed.

Anyway, I’m putting this out here for feedback, from Hawk, from any readers here, and also to my twitter followers. What say you all?

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Tonight marks the end of our one-week experiment of me living with a collar locked on by Hawk. It was definitely an interesting experience.

Despite the fact that I mostly wore it under T-shirts or collared shirts, such that most people would only think it was a chain necklace if they noticed it at all, it was still kind of exhilarating knowing I was wearing a symbol of my submission to Hawk in public. He heavily encouraged wearing it with the lock showing so that some might pick up on the fact that it was more than just a fashion accessory. There was certainly no hiding it in the showers at the gym.

Collared at the gym

Collared at the gym, lock out and proud

Tonight I met up with Hawk so that I could be unlocked. I know he wanted to keep me collared, probably indefinitely. Immediately after entering his apartment he put me in mitts, locked on, and started stripping me. There were many times that I came close to cumming over the next hour or two, but there’s still at least another week before February. Hawk had no such restrictions, though, and added a few photos to his camera roll.

Before parting, he dressed me (still with mitts locked on so I was pretty helpless), bundled me up to go outside (which gave us the silly sense that I was a kid in kindergarten again), and took me out for a walk. He didn’t go as far as using a leash, but that may come in time.

Now since its winter, I’m sure 99% of people thought nothing of the mitts I was wearing. I doubt anybody noticed the locks. But, it’s an interesting thing to walk that line between public and private, to experiment with exposure and kinks like that. I have no interest in making other people unwilling participants in my fantasies. I don’t think wearing a chain around my neck crosses that line, but maybe a leash would have, and while there are some obvious things that would cross it, it’s still hard to see where that line is. At least I know there will always be plenty of contexts (i.e. where I know the audience is more appreciative) where boundaries can be pushed a lot further. And everywhere else it’ll just test Hawk’s creativity to see how he can make me keep feeling like his good pup.

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At about 5 pm today I got this text message from Hawk:

Hey pup, it’s time to lock a collar on you. Long overdue.

Immediately my heart jumped and I started thinking of all these reasons why I couldn’t, who might see it, what people would think, blah blah blah… but very quickly I knew that he was right. It was time.

Within about 2 hours of receiving that text, I was on my way to meet him and I heard the click of the lock with almost no discussion.

We’ve talked about doing this before, and with several variations. One was that I should have one of either the chastity cage or the collar locked on at all times—if I wanted one off for whatever reason, the other would have to go on—or maybe the collar would have to stay on until I trained myself to stay in chastity for at least a week. This first time, though, we’re keeping it simple. It will stay on for a week. Period. No excuses. Collared.

Collared and naked

One week starts now.

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For the entire calendar year of 2014, I am only allowed to cum 12 times. Once per month.

Basically the idea is this: not cumming means I stay horny, and being horny makes me more submissive, more obedient, more in tune with what turns me on, more willing to act on my desires, and makes it way more fulfilling. Despite being an exhibitionist, I’m surprisingly reserved, and encouraging myself to be more open, honest, and active sexually is a major life process for me. A lot of my kinks and fantasies will be laid bare on this site I’m sure. Pun not intended.

The idea came about while talking about my friend Hawk about chastity. I’ve always liked edging, or jerking off for a really long time to build up a bigger orgasm. In November, almost on a whim, I stopped jacking off to see what it was like. I promised Hawk that I wouldn’t cum until he let me. At first it was just going to be a week (already longer than I’d ever gone without jacking off since the first time I had done it) but our schedules just didn’t line up, and it was three weeks before we finally got together. He gave me one of the most intense orgasms I’ve ever had that night.

Having promised to Hawk that I wouldn’t jack off was the only reason I was actually able to do it. I like to commit. The specific idea of only cumming once a month was originally just a hot idea spoken on a hormone high—the thought of how horny and submissive and willing I’d be at the end of each month—but I want to commit to it. Make it real. Make it official. Lock my cock up. (This isn’t a challenge to stay locked all year, but I know from experience how tempting it can be to cheat, so I’ll take any help I can get.)

I’m keeping this blog to keep me on track, and to encourage those ideals of openness and honesty about my sexual side, to stop segregating my sexual and non-sexual lives (in the same way that I’ve been doing with my twitter and tumblr accounts). I won’t describe every sexual encounter or fantasy I have, but I will describe a lot. I’m also going to keep stats on my progress including how long I’ve gone without cumming, how long I’ve been locked in chastity, and how many times I’ve cum so far. Encouragement from supporters will be appreciated I’m sure.

I’ve already cum twice this year (posts coming soon), so I’m starting at a disadvantage. I only get to cum ten more times before New Year’s 2015 (and that’s “cum”, not “orgasm”, as Hawk was quick to point out). Hawk has suggested I might be able to earn extra cumshots by doing particularly daring or ambitious things, but we both agree that those should be very hard, such that I only get one or two extra shots all year (“14 cumshots in 2014” has a nice ring to it) if any at all. More likely, Hawk will be pushing me all year to achieve all kinds of new heights so that each month my cumshot is really well earned. All of those challenges and their rewards will be documented here.

As a final note, though I’m writing this on January 5th, I’m back dating this post to January 1st since that’s when the challenge officially started. Generally posts will be dated to coincide with the date they describe, so that when I look back on this the chronology will be correct (i.e., how much time passed between any two events).

Now on to the fun!

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