One of the interesting sessions I had at IML was very spur of the moment. It was early in the morning – and I was after one last session before I headed to bed. I hopped onto Grindr and discovered 31yo John. For those unfamiliar with IML, one of the benefits of having a host hotel is that sex is pretty much just an elevator ride away. An inconvenient fuck would be having to change from the North Tower to the South Tower. I’m going to be doing some writing on safe sex in some future blogs. As regular readers of this blog will know, I don’t have unsafe sex – but for this session I made an exception when I agreed to blow a load over the ass of a boy who had been getting fucked raw, and then pushing it in with my hand.  I’m not advocating or endorsing this kind of behaviour but it’s something that people need to understand the risks of. I asked John to write up his experience…

John’s Backstory

I’ve been servicing and taking care of the sexual needs of men for almost my entire life; I started sucking cock at the age of 9. He was about 13. He was my best friend. He was my neighbor. I took care of him (and his cousin) on a daily basis until my family moved when I was 12. I didn’t find anyone that needed that kind of servicing until I was 16 – that was the first time I got fucked. Wow it hurt, but I liked it….a lot. Once I had a car, I went out and found cock to service anywhere I could find it – adult bookstores, roadside rest areas, bathrooms at large department stores, etc. It’s either that people grossly underestimate the sexual needs of men, or I just instinctively know when and where to be in order to service the right guys (which if I’m honest, is any guy)

Fast-forward to my early-thirties. I’m 6’0” (~183cm) tall, weighing about 300 pounds (136kg, or 21 stone 6 pounds), HIV-negative (#teamprep), and STD free – I’m a big guy (with a VERY BIG ass, and somewhat in the American gay culture that’s not the demographic that has the highest demand, so I do whatever I can to snag cock when and where it’s available. One of my favorite things to do now is set up in a hotel room, get all prepared for whatever type of use comes my way, post a few ads on dating apps and various websites, and wait for the cocks to come. I LOVE anonymous sex, and I LOVE rough sex – if I bruise, I’m happy. The Leather/BDSM community is the obvious choice for my best luck at getting “what I want” (As a brief point of clarification, I do have a couple “standard” limits – I don’t do anything involving blood, no scat, I prefer no type of feminization, and I’d like to not have sex lead me to the hospital….moving on). IML (International Male Leather) is a huge annual event held in Chicago, Illinois, USA and it’s conveniently a 4 ½ hour drive from my home outside Detroit, Michigan. I had been planning to attend IML for almost an entire year, and engaged in lots of sexual activities that I hadn’t before in order to prepare for what I may be faced with at IML (fisting, pnp, large toy use, bondage, etc)

John’s IML Experience

I arrived in Chicago on Thursday May 26, 2016, got my room all set up, starting posting my ads…and my first day went just ok. Six men came to my room and proceeded to use me how they wanted. I hoped that the following day would be even better – it wasn’t. Only one person came to my room that night, at about 2:00am, and after some awesome intense fucking he attempted to punch fist my hole with his VERY large hand, WITHOUT the use of any type of lube whatsoever. Now, that’s a very physically jarring thing to have thrust (pun intended) upon you. I had such a strong physical reaction that I got a small amount of “dirt” on his hand. This guy flipped out. Instead of washing his hands in the bathroom, he used my bedding to wipe his hand off. He hit me in the face a couple times (I saw flashes of light when he hit me) and proceeded to physically punish me and verbally berate me (loudly….and hotels have thin walls). He kept saying “when I come back you’d better be ready”….I was actually scared. Once I managed to calm him down a bit through letting him submit me to a brutal throat-fucking, after which he promptly left. I began cleaning up my hotel room; as I was cleaning, people were coming back in from that night’s bar-trip. I’ve had a few experiences before this that have crossed the line beyond being sex, an occupational hazard I suppose. I wasn’t going to let some asshole ruin the rest of my weekend. Once the hallway traffic pretty much stopped I called the front desk for new linens, took a shower, got dressed and took a walk around downtown to clear my head. I got up in the late afternoon and got myself all set to service some cock. I really wanted to get fucked, despite what happened the night before. I posted my ads and waited for responses; three men came to me on Sunday. They said they wanted to fuck but just wanted a blowjob. This wasn’t turning out to be the weekend I had hoped for. Checkout was at Noon on Monday and I wanted some fun that would overshadow Saturday night and salvage my very expensive trip to Chicago. I stayed up all night looking for some fun – and I almost passed up what would turn out to be one of my best sexual experiences ever. At 6:39am I received a message:



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Sir walked in and i heard Him start taking His clothes off. i was wearing nothing but a pretty worn out camouflage jock strap, bareback porn was playing on my TV (TIM – my favorite production company). i heard the sound of a glove going on His hand which was my cue to take my first hit of poppers. Sir used my extra-large (and sadly almost unused) can of Crisco and started working on my hole. He ordered that my eyes stay shut the entire time He was there, and the next 44 minutes were surreal. Time seemed to stand still, and fly by simultaneously. Sir was very intent on getting His fist inside my hole. He told me when to hit poppers again, when He was going to really push for 5 seconds (which felt like HOURS), and when to suck His THICK AND VERY LONG cock. (Sir’s dick would ruin an inexperienced bottom; i long for the day He plows my hole with it, even if it means he wears a rubber.) When He ordered me to slide my ass to the edge of the bed, it happened immediately. When He ordered me to move to my back, i did immediately with my arms behind my back (which i hope He took as a showing of respect). Sir had an amazing ability to make me feel both worthless, and priceless at the same time. The way He slapped and punched my ass made me want to do anything possible to please Him. He came so close to getting His fist in my hole, but i wasn’t successful in welcoming his Large Hand in my hole. i wish that i had been able to take His fist, and i look forward to the day that i can make it up to Him. He shot His load on my back, and then pushed it deep inside with His last attempt to be wrist-deep. As i laid on the bed while He started to get dressed, i briefly opened my eyes and almost turned to look but quickly shut them and buried my face back into the bed. He ordered me into some positions while he took a few pictures. The final position was to lay on my back with my mouth open; He put a card in my mouth and ordered me to bite down. i did, and promptly heard the door open and shut as He left. Immediately i wondered what was written on this card, but was too afraid to open my eyes – maybe He was still in the room and was testing me…i wasn’t sure. After about 15 seconds of silence, listening intently for the sounds that someone else was in the room, i knew i was alone. Still – what was written on this card?! It could have been any number of things ranging from something playful to something dark and sinister (face it, there are some really dark sides to the gay community). my eyes opened, and saw it was a card for His site. A smile came across my face followed by uncontrolled laughter – the good kind, the kind of laugh you give when you’re happily surprised, amazed, and even slightly bewildered at what just happened. After getting up from the bed, i did what most would call a “happy dance”. 

That was an experience that won’t be forgotten. The word insurmountable seems fitting. I don’t care what anyone says – I won IML this year!

A couple of other observations – his ass was pretty amazing.  He’s a big guy but his ass is just something you want to spank and punch (not punch fuck, just punch).  I went to bed and slept perfectly.  I hope our paths cross again so I can get my hand into his butt…

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