Missed Opportunities

SAM SHARPE

I enjoyed a game of cops and robbers or cowboys and Indians as much as the next kid. Playing make believe was an essential part of growing up. But never in my wildest dreams did I think 15 plus years later, I’d be asked to dress up as a delivery man asking M, my girlfriend, to “sign for a package”.

Sounds lame doesn’t it? Unbelievable even? Well, it all started because I told M about Greg, a friend of mine who was propositioned by a middle aged woman he was delivering a package to the summer he worked as a delivery boy. Greg described the woman as a “Stifler’s Mom” type (for those of you over the age of 50, think Mrs. Robinson). He declined her advances, but we’ve spent the better part of the last decade discussing the “what ifs” of the scenario.

Anyway, a few weeks after M heard about the story she confided in me that she was turned on by the idea of f***ing a “delivery boy” under these circumstances. Before I could even process this information, M asked me if I could borrow Greg’s uniform. The whole situation freaked me out and just as Greg said no to “Stifler’s Mom”, I told M that it wasn’t going to happen. Like, what was I going to say to Greg; “Dude, can I borrow your uniform, M wants me to pretend to be a delivery boy (like you) so she can fuck a stranger (kind of like you).”

For the record people, all this happened when I was in my early twenties. Trust me, if a woman asked me to make a special delivery today, I’d mug a UPS man to get my hands on his uniform and find out exactly what Brown can do for me.

Anyway, my relationship with M ended shortly thereafter and I subsequently had a six month fling with J, a girl I knew from school. J invited me over one evening when she was house-sitting for her aunt. Soon after I arrived, we got  into her aunt’s liquor cabinet, started boozing and then got straight to the action.

In the middle of a particularly vigorous session, J said:

“Choke me.”

“What?” I said, trying to keep my rhythm going.

“I want you to fuckin’ choke me.” She spit the words out as if her mouth was on fire.

I started to stammer, and before I could collect myself enough to put together a sentence, J barked out some more orders:

“CHOKE ME…I want you to CHOKE ME.”

Never one to say no to a woman, I pressed both my hands to her collarbone and applied light pressure to her neck. She reacted immediately. It seemed like it took mere seconds for her to cum, her body writhing and bucking as I struggled to hang on.

When it was over, I didn’t know what to do, think or say, so I said nothing. Neither did J. We got dressed, made our way to the kitchen, ate some food and then I caught a cab. I spent the better part of my ride home asking myself, ‘What the fuck just happened?’

I saw J a few more times before the school year ended, but we never spoke about the night of the choking or her interest in being choked.  Eventually J and I lost touch, but I ran into her this past summer and she looked as fine as she always did. She’s married now and I can’t help but wonder if she asks her husband to choke her and what other interesting shit she might be into.

Looking back, I regret the fact that I didn’t borrow Greg’s uniform or ask J about her interest in being choked. All I know is that if those kinds of opportunities ever present themselves again, the outcome will be different.

What do you guys think?

Bookmark It