Halfway through my last date with The Executive Assistant, I realized what was missing—a personality. On paper, he checked enough boxes to get himself to the second date we found ourselves on, but in reality, he just...didn’t satisfy. I kept digging, hoping I could unearth something of substance, but all I did was inadvertently deposit his lack-luster all over myself. I even started daydreaming about melba toast and cottage cheese. Yikes. He was rubbing off—and not in a hot way. He had to go.
Outside the chain restaurant he’d chosen for dinner, I dodged his limp-lipped kiss and slithered off into the crowded streets of New York, leaving my days of awkward silences behind me. Ugh. I had to develop a better screening system. Because of the location of said chain, I was forced to trek through Times Square on my way to the train. The blinding lights and dangerously obnoxious people drew my attention in ways they hadn’t in years. I was fascinated by the stimulus. It made me realize I needed something electric. Something to remind me I was alive—I opened Scruff. Scruff is an app for like minded individuals who have, or love men who have, a little facial hair. It also tends to be the container for an...adventurous crowd? At least compared to the far more vanilla Grindr.
The service in that part of town is always the worst, though. 10 million people all trying to text photos on those damn red steps—or of their children with those meth-heads in their knock-off Disney character costumes. I kept waiting for the tiles of scruffy faces to load as I boot scootin’ boogied my way west—out of tourist hell and into the cold, unfeeling arms of the gay-borhood. Once the blinding lights began to fade and the fashion moved from ‘I heart NY’ t-shirts to the black uniform of the city, the loading wheel stopped churning and the faces of scruff-tastic men quickly illuminated my phone. I was in the land of abundance—men within feet of me. I tried to siphon through them as quickly and as best I could. I was hoping I’d be able to make a connection before getting to my train station. Luckily, there were a few stops within walking distance, so if I needed to buy myself some more time I could.
I hit up a few different guys, but unfortunately nothing stuck until I was through the turnstile waiting for the uptown C.
Interesting. Now, sometimes the gays use this ‘mister’ moniker as a coy hello—and other times as an invitation for domination. His profile didn’t give me any real inclination for which way he was leaning, but after the humdrum evening I was running from—coy was not going to cut it.
“Hey, boy. How’s it going?”
Ok, we’re in. And if not IN, at least on a path that side-steps the banal.
“What are you up to tonight?”
“Oh...not much. Just at home right now.”
Ugh. This was going to be like pulling teeth.
“Upper East Side. You?”
“Upper West—we’re not that far. I’m on my way to grab a bite to-go, then heading home”
“That sounds promising…”
“Any other pics?”
Then he sent through a barrage of pictures. Most of them included the standard fair for these sites—a dick here, an asshole there. But the final one threw me a bit. He was standing in front of a mirror kind of...poking his stomach out? It was hard to tell, but it for sure flirted with maternity photo vibes—not a nine-monther or anything, but...within one of the earlier trimesters for sure.
I guess I WAS looking for interesting…
“Do you mind if I ask...what’s going on in the last photo? The full-frontal one in the mirror.”
There was sudden silence from his end as my train pulled into the station. I kept refreshing our chat, hoping I’d get an answer before I embarked on the journey of spotty service before me—but nothing. Hmmmm. Had I offended him? I don’t know how...he’s the one who sent the picture.
As I pulled into the 50th street station I got my answer...
“What about it? Do I look fat to you? Like a fat little piggy?”
Clearly I’d tapped into something…
“Is that...something you want?”
I couldn’t tell if this poor thing was trying to get me to call him fat, or if he was baiting me. These apps are riddled with crazies and I didn’t have the patience for a diatribe about fat-shaming.
“I...do. Is that ok?”
“You want me to tell you what a fat fuck you are?”
I couldn’t help it… Something about his permission to leave the world of J.Crew button downs and enter into something far more salacious intrigued me. I can’t say it necessarily turned me on...but the human psyche is fascinating.
“Fuck, daddy! Please!”
Ok...I wasn’t sure where this was going to go—or how far. I needed context.
“I love that it turns you on so much. Can I ask...why?”
“I don’t know. I used to be really athletic until college. After that, I started to gain some weight.
I didn’t really notice it until my boyfriend told me I needed to lose a few pounds. It turned me on so much. I just...something about it. It really opened up a lot of things for us—sexually.”
“Well...of course I loved it when he teased me for gaining weight”
“But there were other things…”
“Don’t judge me…”
“Ok. So, I used to love it when he would feed me. He would tie me to a chair and shove food into my mouth until I felt sick and couldn’t eat anymore. Then he would untie me and we would fuck. It was so hot.”
I didn’t...I… Look, if nothing else, the universe listens! I asked for something interesting—and she delivered.
“Yeah, that’s what I meant by ‘that sounds promising’ when you told me you were on your way to grab a bite to eat. I was thinking...maybe you could get two meals and…I could come over. You could feed me while we got to know each other.”
I mean...maybe? But I don’t know what kind of food I find sexually appealing. I was planning on picking up Pad Thai—there was no way that was going to do it for me. Pizza? Sushi? Ice cream? Donuts? ...there was something there. There was something in donuts that tickled my taint. I can’t say it got me full-mast...or even half-mast for that matter...but it ignited something.
It flooded from my fingers before I knew what was happening. What was I thinking?
“Oh? You like the idea of feeding me donuts? You like the idea of my mouth and chin getting all greasy with glaze? You want to see me there, helpless, begging you to stop and begging you for more at the same time? Needing you to keep filling me up. I want you to fuck the whole box of donuts into my mouth. I want you to make me take it. Fuck the donut into me.”
“I mean...I guess we could try that?”
“Baby...I am so sorry. This got me so hard. I just shot all over myself.”
“I couldn’t help it. The idea of you doing those things to me!”
And as quickly as it began, it ended. He’d cum before I’d even made it to my stop. I guess it was for the best. I wasn’t ready to go from warm milk and crackers to a dick coated in glaze. I tried to save his profile—just in case I ever worked up the nerve—but his little picture and our conversation had disappeared. He’d blocked me. I figure he was embarrassed...or maybe just hangry.