Selling Chocolate Cake

Let's call this guy Jason... 


Over the summer I struggled to find a job. No one wants to hire someone who sets a date they plan to leave to go back to school.  After countless applications I finally got a job at a
local place that was half Arcade and half Restaurant.  The place marketed itself as a family establishment so generally my days as a server were filled with pointless attempts at flirting with the countless DILF's* that came in with their families.  (Flirting with the DILF's will make another great story sometime.)


Every Sunday the owners brought in a "specialty dessert" that we ( the servers) were encouraged to sell. Our reward was always the same, a free meal.  Let me be honest, the last thing I wanted was a meal at the place I worked, but back to the story.  One Sunday, Jason and his female housemate came in for dinner and a few drinks. At first I assumed they were dating, but after creepily watching the table, it was clear there were just friends.   This caused a tightening in my pants, he was hot, Blonde spiked hair and deep brown eyes, sexy ass hell stubble and an ass that just begged to grabbed. Side note, I did not grab his ass in public, and his ass will lead to hell later, but for now I knew I wanted to talk to him,but how?


Well the chocolate cake duh (I mean did you read the title of this post).  So I quickly grabbed a table tent that had a picture of the cake from another table and made my way to him. I got to the table and needed to somehow hint that I was gay without totally outing myself (ya know, just incase he was a homo-hater). So I casually slid into the conversation that just last night I had been in NYC and was partying at SPLASH,  hoping that my hint of a popular gay bar would set him off. Fortunately it did :).  I casually brought the conversation back to the cake and asked if they'd like to share a piece, they said no (bitches...) but I got an even better dessert that night,  he left his number on the receipt (and a damn good tip to boot.) 


I wasted NO time in texting him, and by no time, I mean literally as he was walking out the door his phone got my text.  Something to the effect of - Nice to meet you, I'd love to suck your dick - ... okay it wasn't that blunt, but pretty damn close "Hey, thanks for coming in tonight, wanna grab a drink" was the exact text I sent him. He responded nearly just as fast "I'd love to, tomorrow at 8, my place?" and so it began....


I really liked this one, so I was hoping for more than just a one time thing. He felt the same way, so we decided to go on at least 3 dates before getting into bed together.


Well, I lasted a date and a half. The second time we hung out I may or may not have blown him,(Okay who am I kidding, I sucked him in the kitchen as he was making my second drink) but that was it. He finished up and we went back to talking. I was a little upset I got blue balled, but again thought nothing of it until the third time we hung out.


I came over after work one night and crawled into bed with him. We cuddled and he jumped on top of me, we grinded our naked bodies together for a while and then I was hoping he'd start kissing his way down, nope, no such luck. So I asked him if we could talk for a second.


I asked " So ... is there a problem with my dick?"
"No... its so hot, nice and thick"
"Thats great... but you haven't gotten close to it...."
"Oh, I don't give head..."
"Oh, thats cool I guess" - Meanwhile I'm thinking... you better be an amazing bottom or were fucked.
"Should I get the condoms?"  he asked.


By this point I'm thinking. We might as well just get it over it, we're already naked and its just sex. So I say sure, go for it.... and this is where the sex for the evening stopped.


Now here is where the confusion came in. I thought he was a bottom, he thought I was a bottom...lets do some basic gay math


Top + Top = Sacrifice ... or no sex


Well we tried the sacrifice thing for a while, hell we actually flipped coins when we started getting into it, Tails, he bottomed... Heads, I bottomed. It worked for a about a week before we both realized we were better off being friends.


at least until  we find a bottom for us to share... or one of us learns to love bottoming. 


I guess I should have tired to sell my Chocolate cake to someone else. 






** DILF = Dad I'd Like to Fuck.  = an older man, usually with kids.