So back in May, my puppy Cockpit took me to IML!
THURSDAY
He booked a room on the Thursday before we flew out at a hotel near LAX. I was greeted with a shuttle which took me to LAX where I found the hotel. When I checked in I was delighted at the room, but then discovered the shower and was floored. It was huge! You could easily have an orgy inside! All of this? Arranged by my puppy. As a special thank you for puppy, I stripped naked, and donned only my aviators and my Sir cover, hiding myself only with the package he asked me to bring along with me which contained his brand new boots. I heard the door unlock and gave him my sexiest smile, and he nearly dropped his bags laughing as he came in the door.
Later that night handler and puppy shared an intimate scene in the large shower, the lights shutting themselves off automatically, and our passion was lit only by the soft blue light coming in from outside the glass block wall. A night I will recall many times, and with a happy smile on my face.
FRIDAY
We flew out of LAX early that morning, and I enjoyed a beautiful view of the world from the skies. Craggy mountain vistas, and miles of flat lands, a patch of sand dunes at the base of a red mountain, acres of clouds, such a gorgeous world we live on! When we landed in Chicago and descended into the lobby I saw someone holding a sign with a name on it using the first initial of my name and my last name after it. I thought "Oh how coincidental...wait..." I looked at Cockpit and seeing his knowing smile, I looked back at the woman holding the sign. It was for me! A few minutes later we were riding in a town SUV to IML!
I love my puppy!
We approached the Hyatt Regency that afternoon and already I could spot leathermen around the hotel, titleholders as well, back patches reflecting the sunlight. We were here! Heading inside, beyond a huge black curtain and a sign stating that the hotel was closed to a private event, my excitement was building! We passed the curtain and headed up the escalator to the front desk to see...not much to see. "...oh...the leatherfolk must be asleep," I thought. However a few muscled bears walking by in street clothes with arms as big as hams got me excited once more! We set up our room, and I then went to meet up with Pup Trigger, a puppy whom I had been talking to for a while online. We headed into his room, which was a trio of rooms all connected and set up by his friends. One to be a sleeping room, one for sitting and visiting, and the final bedroom for play. We sat on his play bed and talked a bit, cuddled, then started to play. He was a lot of fun to dominate, his playful puppy nature, his cute face. At one point I ordered him to strip for me, and I saw that his friends were looking in from where they were laying on the couch in the next room. I said that we had an audience, and Trigger looked over and smiled, I gave them a little wave and then saw that Trigger had paused his stripping.
I said, "I didn't say stop." and his friends erupted in laughter. I can't wait to play with him again, he's so adorable, and I love to make puppies happy. When we finished, I happily visited with his hot and sexy friends, before returning to my own room and to my own puppy. We went out to the city, and admired the skyscrapers, and I learned that in the city of Chicago, panhandlers are issued registration numbers by the government. We ate true Chicago-style deep dish pizza followed by cookies and milk for dessert! All the while admiring the muscled men walking the streets, thanks to the IML Effect on the city! Kinksters were everywhere, I even saw a furry!
That night we went downstairs, me in leather and Cockpit in puppy gear, we met up with Pug who was rocking another sexy dress. Picture requests were very frequent, and we both loved the attention. After a while we heard about a rubber party and decided to try and find it. Still new to the hotel, I got us lost and in the wrong tower, where we happened upon the IML opening ceremonies. We stood at the door and watched as leather men paraded up to the stage holding giant flags from each representing state and region, the pomp and circumstance was overwhelming! Cockpit poked me with a mitted paw and pointed to his bare arm, he was covered in goosebumps. I was starting to get scared and nervous, this wasn't my contest, but the energy was so powerful it felt as if I was about to be called to the stage myself. I couldn't take it! I had to get out of there! I was starting to feel weak! I walked us over to a bench as far away from that door as possible and sat down. I felt as if I was going to break down crying! I was so scared and intimidated! Like a child in a world of adults, the ceremony, the tradition, all of it struck fear into my heart and shook me to my core!
I placed my head between my knees, trying to make sense of it all. The event wasn't even my circuit, nor my contest, why was I so scared? It wasn't me up on that stage, it was the other side of the Drummer split. (As it was explained to me, there used to be one contest, the Drummer contest. At some point the Drummer contest was split into two contests, one contest became more political which is known as the Mr. Leather title. The other contest is known as the Leather Sir/boy/Bootblack contest, and is more play oriented. Of course this is just information as it was told to me, I am not sure of the reliability of this source.)
After getting my bearings, we left and headed into the West Tower to attend the Gear Blast party. Outside we met with my friend Bill from bondage club, who was wearing a stunning full set of SWAT gear! Woof! I met up with more friends, chatted up a bit, then went upstairs for a costume change into my CHP gear. The party was amazing! Wall to wall men, all kinksters, all sporting hot gear! Tons of gear! Muscle men, rubber men, furries too! I met a rhino who let me touch his horn! (Always ask permission before petting fursuiters WITH CLEAN HANDS, those fursuits are fucking expensive and synthetic fur doesn't grow back!) Cockpit pupped around with two other pups, I saw my friends Dennis and Pug, but then soon felt very fatigued and a little sick. Cockpit helped me back to the room, and we went to bed, I had been dehydrated and it had finally caught up with me during all of the overwhelming excitement.
SATURDAY
Saturday morning we ate breakfast in the hotel and were lucky enough to eat next to a very hot, very beefy South African man, who was a very pleasant dining partner.
I was invited to a boy auction that afternoon, which I attended since they were so polite and excited for me to come. It was very amusing, I met boys who were also competing in the Internationals contest in July, plenty of handsome and fun guys. At the last second I decided to join in as well and placed myself on the block. Even before they finished reading my bio, bids were going, I was incredibly flattered! It was then that Cockpit showed up and began to bid against the highest bidder, I was so touched, and soon I was won off the block at a bid of $45. I jumped off the block and hugged my puppy, I told him he didn't have to buy me to have me, but then he said that after seeing some of the men bidding he was concerned. This is why he's my puppy, my shining Golden Retriever!
During the auction I saw a man I had been planning to meet up with that day, KingCorvid, a cute sandy-brown haired pup and a very cuddly, slightly hairy one at that! Cockpit told me to go and play and swatted my butt, and that I'd work off my debt later. I kissed him thank you and I followed KingCorvid to his room and eagerly played with him. I cuddled his soft body, kissing his sweet face, fondling him and holding him close. I tied him up, making him my helpless puppy playtoy. After a short period of dominating him, I prepped him and gently entered his body. I really enjoy topping helpless boys, especially when they're noisy! He made some very enjoyable noises while he was mine! Despite his roommates quietly coming in and out of the room, passing by and observing, I had a wonderful time, in fact it added to the scene that I had an audience! I wanted them to watch. It got hotter, and more exciting, dominating him, listening to his whimpers and moans, and soon I peaked and erupted inside of him!
After slowly removing myself, I stroked him, kissed him, reminded him of what a handsome man he was, and excused myself to clean up. Returning, it was time to please the prisoner! I happily stroked him, kissed him deeply, bit and nibbled on him, made him gasp, moan, and smile, and brought him up until he shot his load all over his hot chest. After cleaning him up, and releasing him from his ropes, I took the time to introduce myself to his handsome roommates. After a little chat, I kissed my date goodbye and left to meet Cockpit down in the Leather Market. As we wandered about one of the bidders from earlier approached me, and asked if I had worked off my debt yet, Cockpit replied that I had only worked off $7. The way the bidder got in my face and invaded my personal space was really creepy when he talked to me, if he had won me and tried anything, well let's just say that I wouldn't have put up with it.
Later that night we came down to the West tower and helped set up for Woof Camp, one of the biggest events at IML, and all thanks to the SF K-9 Unit, as well as the efforts of the volunteers and Brue! The room we were working in was incredibly warm, so I stripped down to my foxxy boxers (boxer shorts with foxes on them, a gift from Cockpit), and at one point we needed doorstops. Feeling ballsy, I went out of the room in nothing but my boxers, approached a hotel employee and asked if we could have some more, her reaction was calm, collected, and all natural. I'm so proud of her, of course I was probably the tamest thing she'd seen all weekend, so a boy in boxers was perhaps a mild sight.
Woof Camp was amazing, a double ballroom absolutely stuffed to the brim with handlers, man pups, and plenty of onlookers and curiosity seekers. Pinatas were thrown to the dogs and absolutely shredded, two visits from the mailman, in a desperate attempt to distract them, the mailman threw squirrels into the crowd of pups, he tried to run but they took him down and I watched as he was overcome by men in puppy gear. He emerged, smiling wide, his pants were shredded to ribbons as he stumbled away.
I went upstairs to take a rest for a bit, and then hurried back to help tear down, I was startled at the change. When I had left, the room was filled with activity, and upon my return everything was over and done with, and only a little bit was left to tear down. We discovered one puppy guest had made a treasure trove of squeaky toys that were tossed out and hid it all under one of the stage platforms.
Returning to the room, and placing Cockpit back into puppy mode and gear, we went downstairs where I grabbed a Long Island Iced Tea and enjoyed the sea of hot men milling about in gear before we grew very tired and headed off to bed.
SUNDAY
After brunch at a nearby restaurant, we returned to the hotel and headed down to the Leather Market to find something to use the Squarepeg Toys voucher Cockpit earned for volunteering at Woof Camp a second year. While downstairs the bidder from the other day found me again, and again stepped too close and asked where I was from. I stepped back and answered, not getting the hint he stepped inside my space again and said he could show me a good time if I were in San Francisco, I stepped back and simply acknowledged his comment. Guys, personal space is important to people, don't try to be sexy like that, if I don't know you and you crowd up on me, it's going to be really negative really fast. Back up please.
We looked at the toy selection on the Squarepeg tables and Cockpit didn't see anything that he wanted, already possessing three tails of his own, he didn't have any want for another, so he offered to use the coupon on me instead! I was so thrilled, I chose my very first rubber puppy tail plug and hugged Cockpit tightly! He always says that I'm going to pay someday, after all the wonderful things that he's done for me, I'd do anything for him. Taking Cockpit upstairs, we headed to Master Richard's room where he had set up a puppy play group which was a little more like a puppy day care. I saw other pups there, looking out the window, napping in the cage, pupping out on the floor, and just having a good time. I left Cockpit there to have more puppy time, and left to fly solo for a little bit. I wandered the hotel, my meetup for that day had to cancel and I was left to my own devices. Heading back down to the market once more, I tried to find something I wanted.
Before the beginning of this trip, Cockpit had me saving up my paychecks, taking small portions out and placing them in savings. Upon check in to the hotel he turned to me and said "Remember all that money I told you to save up?" I nodded, thinking it was time to make a withdrawal and help pay for the room or the airfare. "Take it out, and go find something you like in the Leather Market."
I'm constantly floored by his amazing generosity, his giving spirit, and his acts of selflessness towards others. He's what a saint should be.
While wandering the aisles I found a spanking demo in progress. The sub was being wailed on quite hard, his ass a deep purple and bleeding, his screaming could be heard anywhere in the marketplace. I was talking with a bystander about the possibly difficult aftercare that someone would have to provide to that kind of intense play, dressing his wounds and cleaning up the blood. He was polite at first, then he fondled my ass in an unwanted advance. Guys, seriously, not in the first three sentences. Work up to that, don't grab my ass on the first hello, you become a creepy old man.
Thankfully I met up with friends, and one asked why I was wearing my Sir Cover with my boy title vest. I explained that I wore both to honor the people they represented. My cover was presented to me by my puppy, Cockpit. My vest presented to me by the people in San Diego who decided I should represent the region's leather boys. A little later I departed to the Puppy Daycare to pick up my puppy.
Upon entering, Cockpit saw me and barked excitedly, coming up to me wagging his tailplug. I felt like I had a real dog for a moment, it made me feel so wanted. I leashed him and we said our goodbyes and I took my puppy back to the room where we both lay down for a nap. Me in the bed, and Cockpit on his blanket next to the window. I awoke to Cockpit making puppy noises in his sleep, and I slipped out of bed silently to lie down next to him for a quick cuddle. It's amazing how far he'd gone into puppy space to imitate dog sleep behavior naturally.
We then got dressed, and headed downstairs to the hotel restaurant for dinner, Stetson's Steakhouse. The restaurant was a decadent experience! Led into a beautiful restaurant, we went from the crass, loud world of the leather party scene to a quiet, sophisticated world of hard wood walls, brick, and fireplaces. The more refined and classy side of leather appeared at one table as a Sir was dining with his boy. Both in formal leather. Cockpit and I shared a Caprese Salad, followed by an 8oz Butt Steak served with Au Gratin Potatoes and a Peppercorn Sauce for myself and Cockpit enjoyed a Mushroom Ravioli. The portions, the presentation, the environment, the flavors, I enjoyed and relished every second of it! We had deep conversation, laughed ourselves silly, and really enjoyed each other.
Dessert was ordered, and I had espresso while Cockpit had tea, and then a gigantic Banana Split appeared on the table. Served with fried bananas, and the classic ice cream scoops of Chocolate, Vanilla, and Strawberry, covered in pineapple, toffee chips, walnuts, and of course whipped cream and cherries. After we dug as deep as we dared into the ice cream boat we were presented with Chocolate-dipped Strawberries served in a bowl of dry ice, spilling mist all over the table. I'm feeling stuffed all over again just thinking of it all!
Cockpit had me sign for the room, I opened the book and quickly shut it again in shock. Oh my universe. I couldn't be more grateful for his immense generosity. He had been taking care of the entire trip. Meals, room, plane fare, drinks, and all he asks in return is leash time.
Any time, my puppy, you want leash time, I will give you all the leash time you want. All you need to do is tell me that you want to go for walkies. I love you! I would put my life on hold to take you out for a walk after all the wonderful things you have given me.
After we left the restaurant we needed to work off some of the meal, so we took a nice long walk around Chicago, saw breathtaking views of the city skyline, police boats on the lake, we visited the shops at Navy Pier, and had a wonderful walk in the city night. Upon our return we doubled over in laughter when we found a discarded condom on the corner not a block away from the hotel! Stay classy gentlemen!
Returning to the room, I was contacted by another man I had been talking to online, Jimmywolf, and upon Cockpit's encouragement, invited him to come to the room.
A handsome man arrived with a duffel bag, and after the initial meet and greet, excused himself into the bathroom. I changed into my own leather, and waited excitedly on the bed, Cockpit keeping a watchful eye from his blanket. From the bathroom emerged the Dark Jackal.
Harness boots, leather pants, long industrial rubber gloves, and a black Jackal gas mask staring down at me with black eyes. He dominated me as a beast from the shadows, firm, straightforward, masculine voice, orders telling me to lick his leather boots, worship his gear, chemical gloves grasping my mohawk firmly, caressing my body lightly and sensually, then his rubber grip on my neck, Cockpit at the edge of the bed, ready to bite like the loyal dog he is. Eventually the order came from inside the sinister mask.
"Cum on my boots, boy."
I excitedly followed his demand, and worked myself up to exploding all over his beautiful black leather harness boots! I was then ordered to clean them...with my tongue, I eagerly did so, and enjoyed it very much. He then allowed me to don his gear, and I became the Dark Jackal. It felt amazing, slipping on the rubber gloves, putting on the Jackal Gas Mask. I felt incredible, dark, intimidating. Cockpit really liked that. I especially loved the feeling of the dark rubber on my naked skin.
After the handsome Jimmywolf took his leave, we headed downstairs ourselves and walked outside the hotel. We found Pup Apollo and I separated from Cockpit to let him play with Apollo for a little bit while I played "Where's the sling in the window" with some friends of mine. Returning to the pups, I gave Cockpit the rest of his water bottle that I had with me, his Canadian blood doesn't let him cool off very well at all, so he needs more hydration than a regular pup. After he was finished, he played with the water bottle until he smashed it flat on the ground, where he grew bored with it. I bent down and asked, "Are you all finished with it?" He responded with a dismissive "Arf" and flick of his paw.
I was stunned. No longer was I a dominant handler at the top side of a leash, I was now a boy in service to dogs. I couldn't help but burst out laughing. I was then given permission to hold Apollo's leash, and taking up Cockpit's, I assumed the role of Dominant Handler once more. It felt invigorating! Two hot pups, one on each hand, walking through the lobby of the Hyatt Regency at IML! In all honesty I felt like the image of envy for some of the hot guys there. That feeling of being a badass. It's a thrill! It's what I secretly enjoy, being admired, being that "Mr. Awesome" for people to look up to, to enjoy looking at, to want to imitate. It's a short little ride, and I do my best to be conscious of it so as never to become an arrogant, conceited prick. I've seen that, and it disgusts me.
From there we said goodbye to Apollo as we headed up to our own room, and then went to bed, as it was insanely late.
MONDAY
Cockpit and I met with Pup Phoenix and toured the Handcock Tower and its breathtaking views of the city of Chicago and the lake. After the tour we headed back to pack our bags. I grabbed the leftover strawberries from last night's dinner and while we were downstairs, I saw Pug. On our way out I asked her if she liked chocolate dipped strawberries and before she could finish saying yes, I shoved them in her hands and didn't give her the chance to refuse, waved good bye and met Cockpit at the cab.
Arriving early at the airport, I saw an adorable TSA agent when in line for security and opted out of the body scanner (those things creep me out and if they want to see me naked for national security, they need to hire cuter boys to strip search). Unfortunately I didn't get the cute one to pat me down, but it's a free groping so there's no reason to complain.
Cockpit treated me to Jamba Juice, and soup at Wolfgang Puck's in the terminal, after a visit to the private lounge of the airline we were taking, we boarded into First Class, another one of Cockpit's gifts!
After a complimentary cocktail of Bailey's Irish Cream, I had dinner of Spinach Stuffed Manicotti, Salad, a Bread Roll, and even wine! Earlier on takeoff the sun was a blazing orb of deep orange fire, then I saw a raging thundercloud in the distance! Lightning surging violently around, thrashing about inside! A mere ten miles away! We flew in decadence, our stewardess was fun and friendly, and the entire trip was just so wonderfully memorable! From start to finish.
Dearest Cockpit,
I am so grateful to be your Handler, and the recipient of such incredible generosity.
I cannot thank you enough!
In deepest gratitude,
Your Handler, Zachary.
Play safe dear reader.
