Blowing My Wad — Part 6: Take a Walk on the Wild Side


This is what happened: I got hit by a truck about a year ago, and I got 500K to compensate me for my bones shattering and for the spinal fluid leaking from my ears. Since then, I’ve burned bridges. I’ve lied about my identity. I’ve isolated myself in a world of booze, whores and holidays. And it all seems like a giant blackout, now. This isn’t an ‘I found God’ kind of story. Though Lord knows if I get my hands on 500K again… This is just the story of how, for one year, I became Dennis Wilson, Bukowski and Hank Moody all rolled into one hot mess.

When you engage in a lot of sex and watch porn addictively, it’s important to keep moving forward so you don’t get bored. So you explore.

Exploration always starts with research. Understanding how users upload content to tube sites is imperative for a successful researcher. Keywords. Tags. These are important things to understand when you are a sex addict pervert. You get better, more precise results when you type in “bigass” as one word and know that typing in “BBC” will get you more specific results for “big black cock.”

I was forcing myself to find something which is an unnatural act when attempting to acquire desire. I needed to find a new fetish… but I didn’t want to force it.


One day, I was browsing for porn videos, feeling burnt out. John Waters’ “Pink Flamingo” was playing in the background and it hit me: Shemale.

The simple mention of the word tranny and a dude masturbating to it makes you instantly some sort of spawn of Satan. I liked that. So I started watching Shemale porn. At first, I realized entering blind and typing “shemale” into a tube site can get you some pretty undesirable results (i.e. dudes that seriously just looked like dudes). I wanted feminine looking women… that just happened to also pack a penis.

I really preferred the Shemale to girl videos instead of guy-girl but it’s tough to be picky when you enter this world. Browsing for lists on the web of the hottest shemales I managed to find about 4-6 I found hot. When saying I found them hot, it’s almost like I have inspected them face, to chest to butt to leg… Oh, and then there’s a penis, too. The penis part was always secondary, but a constant driving force in the turn-on.

Pictured: Shemale with a scrunchie.

After a few videos or so of holding my eyelids open to watch it, I slowly eased the tension on my eyelids until I was actually watching shemale porn… enjoyably. It’s amazing to me how some of these transexuals can look so much like a woman (especially a female pornstar).

“I wanted feminine looking women… that just happened to also pack a penis.”

I wanted to try it out. I wanted to hire a shemale escort. But this had to be the real deal. I wanted to find a legitimate tranny who had been deemed hot by others. So, of course, I got drunk and high and found an “elite escort service that catered to people seeking transexuals.” The Ladyboy Company.

I perused the pictures on the site and found this British tranny who I thought was pretty hot. Doable. Also, I actually had never been with a British chick or a tranny so it was a good kill two birds with one stone sorta thing.

Let’s just call her English.

When English showed up at my apartment, I’m not going to lie, she looked like a sexy pornstar female.

“Where do you want my cock?” she asked.

Everytime she said “cock” I could see the spelling go to “caulk”,  like a cartoon bubble, and it made me think of Wayne Rooney applying caulk to a baseboard. Strike 1.

“I need a moment. You can make yourself comfortable on the couch.”

I slipped into the bathroom, peeking out the door as I closed it… and I caught a glimpse of the bulge. I locked the bathroom door. Drank heavily. Tried to psych myself up. For all I knew fucking Freddie Mercury was blaring somewhere right at me. I drank. Tried to psyche myself up. The booze and Freddie combo gave me courage. I opened the door.

“This dick ain’t gonna stay hard all night. Unless you got boner pills. You seem like a boner pill kinda man,” she said to me.

I did seem like the boner pill kinda man. So I locked myself back into the bathroom.

English’s dick was bigger than mine. The fact that this he/she looked better than me as a she and was packing more heat than me as a he made me feel emasculated. Strike 2.

“I want your caulk, little man. Get you cute caulk out here now!”

I popped a few Cialis. I drank a lot more booze and now Marc Bolan and Freddie were screaming all distorted at me in some weird glitzy sleeze glam tune. I shook it off. Opened the door.


English was standing right there, like a boxer, and we were nose to nose with our junk. Then I caught a glimpse of nipple hair. And I swear I saw English’s five o’clock shadow. I saw too much man in her and I knew I wasn’t turned on. English wasn’t for me. Strike 3.

I told English I was sorry and that I’d pay her. She used my shower because I guess I was in the bathroom so long that she ended up masturbating onto my fancy rug. After she dried off, re-dressed, and gathered her things, English said to me: ”Little man… you need a coma.”

“A coma?”

“It’d be a vacation from yourself.”

English kissed me on the cheek and left.

Part of me did want a coma.

But I needed to explore these fantasies. I had a period of strictly seeking BBWs. I tried the 60 and older thing. Vegans turned me on for some reason.

At the moment with English, I felt like I was letting down some idea I had on sexual freedom and philosophy. That I’d chickened out. That I was a fraud. But maybe I just found my boundary of what turns me on. And who knows. Maybe when I’m 80 English will be my thing.

Though — to be fair — I always said their are two guys I’d let me fuck me. First is David Bowie. He’s practically an anamorphic reptile so it almost doesn’t even count. But the second is Neil Young. Which I imagine would be dicey depending on what time period I got him: After The Gold Rush or Ragged Glory period. Could get rough.

I think it’s important to experiment sexually. It’s like how we should all take LSD. Expand our minds. Know what kink does and does not work for you. Makes us better lovers to not be so damn afraid to explore sexually. Stop being ashamed and dig in the bowels of the inner kink. It’s liberating. Penis. Vagina. It’s all the same. We’re just all fucking animals.

Lou Reed “Walk on the Wild Side”


Related on The Smoking Jacket:
Blowing My Wad Part 1: How I Got Hit By a Dodge Minivan and Pissed 500K on Booze,
Whores, and Designer Furniture 

Blowing My Wad Part 2: Chicago Whores 
Blowing My Wad Part 3: 2 Weeks with Pornstar Maggie May 
Blowing My Wad Part 4: Muerto in Bocas Del Toro 
Blowing My Wad Part 5: The Wonder Years