One of the guiding principles of my practice as a sex educator is that I’ve done the work, albeit really messy, so that you don’t make the same mistakes that I’ve made. Learn from me so that you don’t hurt yourself because, girl let me tell you… I have been in many sticky situations and having many partners does not a good slut make.

As of this writing, I have been invited to many podcasts to talk about gay men’s sexuality and anal sex. Every time I talk about this I am reminded of a story, a dark tale of love, loss, and lubrication. Anyways, here’s a story of how I lost something inside my ass. An anal anecdote if you will.

For those of you that know me, you know I like them big. It’s not a must-have, but I can take a pounding like fresh cut tenderized meat at the butcher. I have claimed for myself the title of the tightest gapingest hole in the Greater Toronto Area, and that is something I will take with me to my grave. I challenge you to find another slut that has a hole as huge and as tight as mine. That said, there’s this guy that I’ve been fucking for quite some time. Let’s call him Brian. He’s got one of the most beautiful asses I’ve ever seen. An ass so tight you can bounce a quarter off of it. To add to that, he has one of the biggest cocks I’ve ever seen. It’s so big it would bring that scene from Sex Life to shame. Brian’s birthday was coming up, and up until this point I’ve been topping him. So as a treat, I wanted to bottom for him considering that we’re both versatile. Needless to say that the preparation process for anally ingesting an elephant trunk of a cock is going to need lots of warming up.

I should note that at this point in my sexual journey, I wasn’t really super experienced with taking cock that huge. Yeah, I can power bottom a guy’s dick until it falls off, but most of the dicks I’ve taken in were on the more average side. Brian’s was a literal third leg that it’s basically a medical phenomenon. To prepare for my mission, I bought myself a set of butt plugs. And not just any butt plugs. I bought butt plugs that were a nice solid stainless steel with a Swarovski crystal at the end of it. I’m a boujee bitch, and I wanted to make him feel special. I did all the research I possible could when first wearing a butt plug; make sure to use lube, buy a butt plug with a flared base to keep your ass from swallowing it, all that jazz. Trying to make sure that I would be loose and warmed up enough for him, I started my preparation seven hours early which, in retrospect, could be where I went wrong in the first place. I situated myself in front of my mirror and assumed the position where I had my legs up in the air as if I was in the delivery room except something was about to enter me rather than exit. With one big inhale, I shoved that plug inside my bum like it was my job. Believe me when I say that even if it felt like a constant need to shit, having a crystal peek out your ass looks really fucking pretty.

With a plug in my butt and a song in my heart, I made my way downtown to my well-endowed prince. You would think that the commute there would be quite awkward considering the situation, but you would be wrong. I had to take a bus and a train to get to where he was and both trips had bumpy roads and rickety tracks. It was quite interesting to gauge how my body would react whenever the vehicle started to shake. When the bus went over a pothole, I would shake in my seat and squeeze my knees. A sweet old lady beside me thought I was having an anxiety attack and tried to calm me down. Little did she know that I needed a cigarette more than anything. On the train ride, the tracks were quite old making the train shake a bit. It was at this point in my trip where I started letting out small quiet moans and sweating profusely which was an interesting sight considering that this was in the winter and people were thinking something is definitely wrong with me if I take my jacket off in the snow.

After a grueling 1.5 hours of public transit, and I mean grueling in the best sense of the word, I finally made it to Brian’s. As he opened the door he locked his lips on mine, and we couldn’t keep our hands off each other. The clothes were coming off faster than we could say hello. I tried to get a word in to at least say “happy birthday” but his tongue kept my mouth shut. Him shoving his tongue down my throat and feeling his rock hard cock poke through his underwear and thrust in to my pelvis made my asshole squeeze tighter around the butt plug. I really couldn’t contain myself and I needed to tell him about his gift.

I was able to push him away for a brief moment to tell him, “I have something for you. I know you’ve been wanting it for quite some time now.”

His eyes lit up like a kid in a candy store and said, “Oh boy! I’m excited. Do I have to unwrap it?”

I replied, “Yeah, I hope you’re ready.”

He was so cute with the way he jumped up and down like he’s being rewarded with a new toy. I proceeded to undo my pants and stripped naked for him being mindful of the plug still inside me. And with an Oscar-worthy striptease performance for him, I bent over to show him my butt plug.

I asked him, “Do you like it? I picked it out just for your birthday!”

He replied, “Wait sorry. What am I supposed to be looking at?”

“What do you mean? I bought a butt plug with a crystal because I want to bottom for you. Don’t you like it?”

“Sorry babe, but I don’t see anything.”

WHAT?! WHAT DID HE MEAN WHEN HE SAID HE DOESN’T SEE ANYTHING? I CAN FEEL IT IN THERE!

“What do you mean you don’t see anything?! I can feel it in there!”

I reached around to try to locate the missing toy, and it was nowhere to be found. The butt plug was lost. My asshole swallowed my butt plug. Flared base and all.

“Fuck. It’s inside me. Oh my god, Brian, it’s inside me! What are we gonna do?!”

“Babe it’s okay. We’ll get it out of you! I guess this is the unwrapping, huh?”

I shoved his shoulder. “Stop that. This isn’t funny. I don’t wanna go to the ER and have to explain myself. Oh my fucking god this is so fucking embarrassing.”

Brian tries to calm me down. “Tim it’s gonna be okay. We’ll get it out of you. Just lie down and relax.”

Gathering my thoughts and trying to keep myself from having an actual anxiety attack, I lie down on his bed and assume the position. Again. This time something is really gonna come out. He lubes up his fingers and starts digging inside my asshole like a gold prospector. He makes a hook shape with his middle and index fingers and enters me like I’m a turkey ready to be stuffed for Thanksgiving.

“I can feel it. I can feel the tip, but I just can’t quite get my fingers around it. You’re gonna need to push.”

So we’ve really come to this. I actually have to “push” to get something outside of me. This is it. This is my lowest point. I don’t know how I could ever face him after this. What could possibly make this day any worse?! I did as he said, and I pushed as hard and as long as I can.

“Oh…looks like you’re peeing.”

I spoke to soon. This day can get worse.

I screamed, “FUCK! I’M SO SORRY! AND ALL OVER YOUR NEW WHITE SHEETS!”

He reassured me, “Tim, it’s fine! For what it’s worth, I think it’s kind of hot. It’s like you’re squirting because I’m fingering you.”

I’ll admit it was kind of comforting to hear him say that, but I have truly brought shame on myself and my family and my friends. How could I ever live with myself. This is so humiliating. I just wanted this day to be over. I tried to push again in the hopes that this last grunt of effort will save me a ticket to the emergency room.

“Ah, got it! I have my fingers hooked on the base.”

Oh thank FUCKING god.

“Alright now I’m gonna pull it out. Your hole is gonna stretch so deep breath, okay?”

I push one final time and with bated breath, I feel my hole stretch to its limits waiting for the all-clear.

“Got it,” he says as he waves the wayward anal trinket in victory. “Are you okay?”

“I’m not really sure how to answer that considering I just had the whole plug inside me and I pissed all over your sheets.”

I’m truly ashamed and there was really no coming back from this.

“How about I fuck you until your legs go numb and we can call it even?”

So we did. For the next several hours. Until we were two sweaty bodies covered in every single bodily fluid known to man.

And there you have it. If there’s a lesson to learn here, it’s that don’t keep a plug inside you for 7 hours especially if you have a huge gulping hole like mine. And also find yourself a man that’s gracious enough to go with the flow like how Brian treated me. Men like that are hard to find. And even hard to sit on.