IML 2014 - Day 3

Things did indeed start to get better on Day 3. In retrospect, I think there were a few reasons for this.

First of all, I finally got some sleep the night before. Granted, I still went to bed quite late but I was less intoxicated, less unhappy (two orgasms do that!) and had learned from the night before. I was still cruising on the apps (the slippery slope continues) but didn't put too much expectations on it anymore.


I slept in again, yes, but because I was less horny and not trying to hard to hook up, I actually got proper sleep so I felt relatively rested. Also, I had things to look forward to including a session with J.

All of these gave me a different kind of confidence that were not there the first couple of days. This is the second reason. I think that having had two sessions, and the promise of one more, made me realise that I wasn't so much an outsider after all and helps tone down that chip on my shoulder. It wasn't that no one was interested in me.

This realisation helped me ease up a bit and I also came out of my shell a bit. I chatted to some people in the elevators, mingled a bit more at the lobby and for the first time, properly dressed the part without worrying about what people were thinking (in most cases, I think, they didn't care considering how much fetish gear everyone had on).

The final reason, I think was that I had decided to go out of the hotel for the first time since I stepped in (quick meals didn't count). It was always my plan to take one morning off from the weekend to visit the Sears Tower. The original plan of waking up early for it didn't happen, but at least I caught up on sleep.

That was basically what I did the moment I woke up and showered, taking the Metro over. It was a bit late and I joined the long queue anyway, even if they told me it was going to take a couple of hours at least. The line outside the building looked like it was going pretty fast and it did, I spent about 45 minutes before I got into the building and up to the higher level floor only to discover that there was another two hour line.

I decided to leave despite having queued for so long as I had my appointment at 2.30pm and I wanted to get lunch first. After a quick bite, I tried to look for the station to take the Metro back only to discover that I couldn't find it. So I ended up walking back to the hotel which took a while but the walk, too, did me good.

I had some time before my meet with J so I went back to the Marketplace to do some shopping (retail therapy could arguably be reason #4). I ended up purchasing quite a bit - a leather shirt I've always wanted, two kink-themed T-shirts, a leather arm band as well as a grey hanky.

While shopping, I met T who was manning one of the booths I bought stuff from. I had met him the first day while walking around with B (they are friends) but we never spoke. I was very apprehensive - I felt I knew so much about the guy from Twitter, Recon and the Internet in general that I was a bit starstruck.

We got to talking in general and got along really well. Despite that, I was caught totally off-guard when he told me to wait before I left after paying, and wrote down his phone number on a piece of paper and passed it to me. He asked me to get in touch and see if we could get some play going later that night.

I was more than excited - of course I want to play!

But first, I had an appointment to get to. This session was amazing because it was the first time I was in a full sensory deprivation position. I had gotten to J's room and there were a few people in there, one of whom was just leaving. But his roommate N was there together with their friend Z who was just lazing casually on the bed chatting.

I felt a bit awkward at first as I wasn't sure what to do so I just sat there and chatted where I could; I could follow a bit of the conversation. I'm not sure if J realised this, or it was jsut time, but he asked me to slip into my sleeveless rubber wetsuit that I had brought along with me.

I looked around the room and realised that they weren't moving so I just stripped right there and put it on as if it was the most natural thing in the world. I think it was moments like that which made me realise how normal this is for most people and that I've been worrying over nothing.

Still, midway through changing, N and Z decided to go for a walk and leave me alone with J. Soon, I was put into a rubber sleepsack and a blackout gas mask. I felt him strapping me down to the bed so there was no way I could really move in the sleepsack. I was stuck.

It was then that he told me that he was going to put some noise cancelling headphones on me with white noise. It was the most bizarre feeling ever and I had to try very hard to concentrate to keep track of things. I felt him caressing the sleepsack and slowly unzipping the area near my crotch and pull my cock and balls out.

That was as far as I could keep up because I slowly dosed off and kept going in and out of consciousness. The random edging jolted me awake and I'd signal to him everytime I was close. Then I'd start dreaming and then I'd wake up again until suddenly one time, he just kept going and I finally came. A lot.

Spent, I just lay there as he loosened the straps and then took off the headphones and mask only for me to realise that N and Z had come back. They then told me that I was in there for a full two hours, and that they had been back for a while and were talking at normal level but I just couldn't hear. I found out too that Z took some turns with the edging, which thrilled me because I thought that both he and N were really cute.

I would have liked knowing they had come back midway through - it turns me on to be surprised like that - but seeing them after made me want to cum again right there. I was that turned on.

I rested for a bit after and texted T to make arrangements for the night. He was out at the actual competition till late so he said he'll message me when he's back to meet up. After that session with J and feeling buoyant about the whole weekend, that would have been amazing.

But it was not to happen. He texted me a bit from the competition and as he was leaving, but then just went silent. I was downstairs hanging out at the lobby with a couple of friends waiting to hear from him but nothing came through.

So I decided to go to bed even earlier to mask the dissapointment, plus I wanted to really wake up early the next morning to actually finally get up Sears Tower.

I remember being quite melancholy in bed but then reminded myself that I've had three great sessions - including two out of the three people I really wanted to meet before I even showed up that weekend - plus some new experiences including spending some time watching a huge number of pups at Woof Camp and meeting a couple of other people I know from Twitter for the first time.

I went to bed horny and a bit down but knew I couldn't be too disappointed. And there was tomorrow to look forward to.

IML 2014 - Day Two

Day 2 of my IML was off to a horrible start. For one, I was still a little jet lagged but going to bed at five-something AM really wrecked my system. I didn't sleep very good - disappointed from lack of play, intense horniness and well, wearing a CB to bed might have been a bad idea.

I woke up very late in the morning with a bad headache and still dazed from lack of sleep but I wanted to get my day going. I sent a few friends some messages to see what they were up to (as well as a couple of people I was hoping to play with but they had not committed to anything).

B, who had earlier suggested some bondage time over the weekend, replied and said that he might have some time for bondage if I was keen. Obviously, I was. I've been wanting to play with him for the longest time and after all that time of online friendship, I was glad to be spending some time with him again.

I had to grab a quick bite for breakfast first, however, with my state of tiredness, I wanted to make sure I had enough energy for play. After a few exchange of messages - we were going to play in my room but then he suggested his room because there were more gear there - I found myself heading up to his room with my bag of gear and a thumping heart.

We had spoken a bit about interest and limits (well, he knew a lot but I guess it was worth revisiting since we had only just properly met) and I knew that he was going to put me in his sleep sack. He also mentioned that he was with a friend L and if it was okay that he joined in. I love group play like that, especially where I'm the sub, so it was more than okay with me!

But, like how the day started, things didn't go so well from the start. For one, I forgot to bring along the keys to my CB! So, I had to go through the whole arduous journey of busy elevators again (I think I ended up taking the staircase down) and up again just to make sure I got some decent play.

The session was pretty short, but really fun. We weren't alone - two others were in the room next door and very loud. It was a pretty hot environment - I've always fantasised about spending some time together with a bunch of kinksters in a room and different people just doing their thing, some playing, some chatting like a good bunch of friends.

It didn't take me long to get naked and into the sleepsack. B put a neoprene hood on me, to go with the neoprene sleepsack, and very soon I was immobile and totally encased except for my CB hanging out. It soon came off and there were lots of teasing of my nipples and cock, edging me but not letting me cum.

The session went on for about an hour, which would be a long time for edging, but it felt pretty short. The problem, going back to mistake #2 I mentioned in the previous post, was that I hadn't cum in a few days and had warned B of this. I'm not sure if he was being particularly careful about it, or that it kept playing on my mind, but I spent more time worrying about cumming too soon instead of just immersing myself in the experience.

When I finally came it felt great, but I'm also the kind of person who just have a good nice orgasm after some days of denial, but it really was the second orgasm that blows my mind. Still, it was pretty hot listening to B speak to L about me while teasing me, suggesting locking me back up in the CB among other things.

After I came, and had the hood removed, I realised the other two guys from the other room were also there which was pretty hot. I really enjoyed the experience - especially at the hands of B - but I did leave wishing it had gone on for longer.

As we left the room altogether, we bumped into another friend of theirs who said that he was hosting a bondage afternoon of sorts in the room and invited everyone to come along. I bade farewell to them at the elevators as they were heading to the marketplace and a quick lunch, while I wanted to get a quick nap to make sure I had more energy for the rest of the day. Mistake #6.

For one, I crashed and didn't wake up till past the time the bondage afternoon was happening. I did text B to see if it was still going on and, going back to my insecurities, was hoping he'd ask me to join in but he just spoke about what was happening. I didn't feel it was my place to invite myself and wasn't sure if I was included in the invite in the first place. All these thoughts played on my mind so it messed me up pretty bad.

So I did what someone on the slippery slope would do (mistake #5), I wasted the rest of the afternoon trying to cruise someone to play with, the horniness stemming from a lack of orgasm number two driving me into insanity.

I sent a tweet then that read: "Expectations vs Reality. Rookie mistake." It really was a mix of the post-chastity downer, ridiculous expectations of how sessions should be and kicking myself about missing that afternoon session (I didn't even really need to be tied down, I just really wanted to belong).

After a few hours, I managed to hook up with F, who had messaged me a few days before I made my trip. Truth be told, I wasn't terribly keen to meet him because he seemed a bit eager (a trait that usually ring bells in my head, ironically because I can be pretty eager myself) but at that point, I thought, what the heck.

It turned out to be a good decision - F was a pretty nice guy, and I loved his rope bondage. We had slightly more time than my earlier session but he had dinner plans so it wasn't too long either. But I was nicely roped into a frog tie position and edged for a bit before I was allowed to cum.

When he left, I was feeling my better about myself and in better spirits having managed two sessions in a day. It still wasn't enough but it was hell of an improvement from Day 1.

So I made plans for dinner with A, and his friends. We had a good time at dinner before heading back to the hotel for more drinks. His friends - one of whom is J - were staying at a different hotel so they were going to change first so A and I went back to the hotel and changed as well.

That night was spent at the lobby and a lot of flirting with J. In the end, we ended up in my room. We were geared up but it look set to be a night of just regular sex - which was more than fine with me, he was quite hot. It was hot making out with him and playing a bit but we didn't go very far as he wasn't very sober and let's just say, aware.

I did a bit more online cruising before bed but decided that I didn't want the same thing from Day 1 happening again so I turned the devices off and went to bed. I slept much better than I did the night before. Things were starting to look up.

IML 2014 - Day One

I am very aware that it has been almost four months to the day since IML and as such, the accuracy of the following few paragraphs might have been compromised.

The truth is, following the last statements I made in the previous post as a disclaimer for this series of upcoming ones, I was afraid to revisit those days for fear of crumbling emotionally.

Then, the past few days happened, and I crumbled anyway. So I had a thought - made a decision, rather - that I would embrace the experience and appreciate that for four days, I got to be who I was, as opposed to being afraid it would remind me of those moments.

Because the truth is, those moments happened and they were quite an experience. And if I'm going to be stuck here where I am, then I might as well appreciate what little of "the world I belong to" I can get.

One Day One, that world lay behind the doors of The Marriott Magnificent Mile, in a city I had never been in my life. I had arrived a couple of days earlier to soak in the city - I have a wanderlust that needs as much pacifying as my itch for kink does - and ordered an Uber car early that morning to check in.

I already knew that some "friends" (people I knew online, but have never met in person) were there. I had been invited to hang out the night before, but I declined - a decision, I think, I will continue to regret for a long time.

As I dragged my bag to the entrance, I was stopped by a burly man asking, "Are you here for the event?" I wasn't expecting such a question and just muttered a, "Yeah" - it didn't occur to me that the next four days was going to be an "event".

Walking through the doors, nervous and excited at the same time, my senses were incredibly heightened - I'll be this is how Dorothy felt going through the gates to Emerald City (incidentally, did you know Chicago has a park called Oz and there are statues of Dorothy and all her friends scattered around it?).

I tried not to stare as guys (some of whom looked like they just woke up) in gear were mingling around the lobby area. Because some of the current guests haven't yet checked out, the space was still being set up but a bright, sparkly receptionist brought me out of my daze.

She was chatty and extremely friendly, which put me at ease, until she said: "You're a little overdressed." I was in a pair of jeans and T-shirt, holding on to my leather jacket. I must have blushed 50 shades of red.

In my room, I took a while to settle in. Settling in includes taking pictures of the great view, looking at maps of the area to see where I can hide and well, checking Grindr and Recon out. I have never in my life seen such activity on those apps. I was in heaven. And this was my first slip on the slippery slope of sexpectations (mistake #1).

But it wasn't all cruising. I wanted to get in touch with people on Recon and Twitter to let them know I've checked in.

"What are you wearing?" I asked my friend B, who I've known for several years. I was most excited to see him because I feel we've built a nice friendship over the years, which included periods where he would keep my in chastity remotely.

We finally met in the marketplace, after I spent about an hour alone roaming around trying to soak it all in. I was in a pair of jeans, T-shirt and my boots, the only "gear-like" thing I had on other than the CB6000 I put on when I first got to the hotel. I hadn't cum in a few days in anticipation of the event (mistake #2), and thought it'd be fun to put it on.

I hung around with B and met some of his friends. It was a bit awkward. We hadn't met before so I really loved the hug but found it hard to fit in. It was more me than them, I was extremely self-conscious and I kept asking myself if B was just being polite or if he really didn't mind me hanging around them. I hung around anyway.

Mistake #3 was deciding I needed to get a jacket when everyone decided that it was time for lunch. They didn't have much time so it had to be quick, but a flood of people had started checking in so the elevators took forever. By the time I was heading back down, I had gotten a message that they were going to head out first and I was welcome to join them.

Except that I didn't know the area at all and Google Maps took me to two different outlets and I still couldn't find them. I had walked around, rushing to make lunch, for over 30 minutes by then and so I gave up and grabbed a bite from somewhere nearby before heading back to the hotel.

I went back to the marketplace for a bit but in the end, just headed back to my room to rest (and go on Grindr and Recon - the slippery slope continues) until my other friend A arrived. I let him settle in before we caught up in the marketplace and then had some dinner. I was much more comfortable with him as we were actually physical friends. I would end up being extremely grateful to have A around for the next few days.

A was going to head to some event which I wasn't too keen on so we went back to our rooms. At this point, I got to catch up with S and A2, whose rooms were literally just across from mine. We hadn't met before but chatted often on Twitter.

I wasn't sure if I wanted to head down for GearBlast because I wasn't sure I had enough gear. I'd already been wearing my leather trousers and boots in the evening and my rubber suit doesn't work with the CB.

S decided that he'd let me use his rubber shorts and rubber T-shirt. The shorts fit perfectly, although the T-shirt was a bit big but I had come all the way and they weren't going to let me not head down for some parties.

It turned out to be pretty nice. Different bunch of friends where there. B and A were there with their friends, and of course, I was with S and A2 with their other friends. Eventually though, everyone went away to do their own thing (read: play) and I had no plans so I went back to S and A2's room for more drinks and drinking games.

I was about to leave at some point in the middle of the night when we got attacked by a pack of pups - we had left the door latch undone for some reason and some people took it as an open invitation.

It was most interesting. I have met pups in my life but never really engaged with them much but this was about 10 of them, drinks in hand, all geared up and very excited. A2 and I just stood back and watched everything unfold in the room - it was quite a sight! I really loved that everyone was so relaxed and non-judgemental in there.

I made the mistake (#4) of trying to befriend a couple of them (I even developed a pup crush on one - R) though - I'd learn over the next few days that people who are drunk don't remember you when they meet you next.

Eventually, everyone left and I popped back to my room. By the end of the day, horn was high and I was feeling a bit down from the fact that I'd been there for a whole day and was nowhere closer to any play at all.

I stayed up really late, till almost 6am, trying to hookup which became mistake #5. In four days, it never happened.

I wish I could say that I slept like a baby, but between being completely tired, horny and being excitable from the whole day - it wasn't very good rest.

Still, I had a few days to look forward to. B, who I wasn't sure wanted to play in person or not before we met (I didn't want to be presumptuous), did mention some time earlier in the day that he'd like to have me restrained (which made me very happy). But as is the situation at IML, very few people actually commits to plans ahead of time, especially if you're new friends, so I had to go to bed wondering if my next few days would be exactly like day one - horned up, a little bit sad and most of all, not quite sure what was going on.

IML 2014 reflections - The first post

This post is probably more a disclaimer than a story. It is exactly a month today that my IML came to an end (as you will see in my later post, it ended a day earlier for many other people - much to my dismay) and I have avoided talking about my experience to many people.

This was for two reasons:

1. I was still processing the whole experience.

2. I found that the things I was saying to people who have asked to have come out as negative, and I didn't want people to think I didn't have a fantastic time because in many ways, I did.

But as with most things in life, I wished I had done things differently. Although my journey into kink goes back more than two decades, I still grapple with two major things that have caused me a lot of setbacks and disappointment - my lack of trust in people and my insecurities.

So, as I spend the next few post reliving one of the most momentous moments in my kink life, there will be many references to unhappiness, dissatisfaction and more. What I need for anyone reading them - especially the people I met and have befriended - is that I appreciate that the fault lie directly with me.

While I make comments about how I wished people had done things, responded to me or offered things differently, I am more than aware that I have no right to expect it of them. Especially since I never really told them how I felt. They had no way of knowing.

My highlights were really meeting old friends, online friends and new friends. It sounds cliche but coming from a background where I have so few friends who know about my kinks, let alone are kinky, I really appreciated being able to share my life with like-minded people. The play sessions were equally as amazing (although I do wish I got more play and different types of play as well).

And of course the shopping. But I think the one thing I am most grateful for was that for four days, I could just be myself, never mind that it took me almost two days to actually "be" myself.

Having said all that, I'm not sure if I will go back for another IML. Having a downer from four days of being oneself is one thing, but having a downer and then coming back home to a place where everyday is a kink downer is another.

For wont of being dramatic, I don't know if my emotional wellbeing can take it. I thoroughly enjoyed what IML offered me, I just don't know if I can leave it all behind the way I was forced to again.