Before I can say anything, she pushes me against the wall and we start to make out.

I have a lot of great memories from being in a fraternity here at Clarkson. Still though, the best one that keeps coming back is the one that happened when I wasn’t even a brother!

Spring semester of my sophomore year, I was pretty interested in this fraternity. I had gotten to know a good amount of the brothers and they seemed like chill guys.

On a warm spring afternoon after working out with one of the brothers who originally got me interested in the fraternity, he let me know that their spring formal was that night, in Montreal. Every brother was allowed to bring one other person with them… but he didn’t want to bring a girl with him (he said it’s more fun when you bring a drinking buddy). So next thing I know, I’m in Montreal, dressed up in a nice suit, getting sloshed on free drinks and enjoying mozzarella sticks.

The whole time that I was drinking with the brothers, there was this one waitress we kept noticing. She was older, but one of those handsomely beautiful types. You know, the ones that look gorgeous even when they’re older. We had caught each other’s eyes a few times, but being that I’d only put down 5 or 6 drinks at this point, I didn’t have the courage (or the inhibitions) to make a move on her.

I decided to up the ante and ordered a long island iced tea. The bartender was a nice guy but this had to be the shittiest l.i. ever. You know a good l.i. when it tastes like an iced tea, not having a strong taste of alcohol. This one was so strong of alcohol that I was pretty disgusted by the bartender’s lack of ability. I’m in Montreal, I’m at a nice formal and I can’t even get a good l.i.? That’s bullshit!

Angry at the situation, I distanced myself from the crowd and sat alone at one of the tables, holding my poorly-made l.i. with a scowl on my face. Next thing I know, I feel a light touch and this waitress that I’d been talking about earlier is like “Is everything alright, hun?”

I let her know my displeasure at the fact that the l.i. sucked. She took one sip of it and agreed with me. She grabs my hand and takes me to the bar, where she makes one herself...“just for you” as she put it. I took one drink and damn that was more like it. I sat back at the table with this waitress and chatted it up for a bit. It didn’t take long to finish the l.i. She made me another one and we were back to talking.

As I found out, this waitress was a MILF. She lived in Connecticut and was separated, but had 4 kids. Don’t ask me how she ended up in Montreal, I wouldn’t know. I asked how the waitressing gig paid and she let me know it wasn’t so great. It was at this moment that the combined alcohol of the previous drinks and the 2 l.i.’s decided to blitz me out of nowhere. I recovered my composure from the alcohol just in time to issue what is to this day both my greatest and stupidest line ever:


“Well, that’s a shame. I could help you out a little bit with that, but you’ll have to do something for me in return.” (wink wink)


OK, so I was drunk and wasn’t being serious...in all honesty I expected her to be disgusted and walk away. But to my surprise, she asked me what I had in mind. Again, another brilliant line: “Oh I think you know what I have in mind.”


She smiled and told me to follow her. I can say here that I said that last comment not really knowing what I was thinking, and not really sure what she had in mind. As I followed her, we left the formal area and next thing I know, she leads me into some small room that looks like a coat room or an employee break room or something.


Before I can say anything, she pushes me against the wall and we start to make out. She had a great taste, like a refreshing cold margarita but without the alcohol-ness. Without even breaking eye contact she undoes my belt and pulls my pants down. As my pants go down she does too, and next thing I know she is humming away on my cock. Now I haven’t gotten a ton of blow jobs in my day, so I’m not exactly the expert on what’s good and what isn’t. But I can say with honest conviction, that this MILF took the cake.


She looked up at me and had this look in her eyes like a puppy dog, and that just turned me on more. As she finished, she was even good enough to swallow it all!


After we both cleaned up I took out my money clip and thumbed 4 American 20’s off to her. She tried to refuse it but I told her to get herself something nice—or some stupid line like that. Back at the formal area, some of the brothers had an idea of what had happened. When I told the story, they all congratulated me on my MILF job.


Next semester I got a bid and accepted. I’ve had some great memories since then, but in the end my best one is still the one that happened during that formal in Montreal.