My Worst date ever: By Sweat Shop Sissy
March 23, 2007Entry 1:
My worst date ever occurred while I was still living with the mother of my son. We had decided that even though we couldn’t stand the sight of each other, we would continue to cohabitate for the sake of the child. It had been about a year since we’d had sex when I decided I was going to start dating. I told her that’s what I was doing and her attitude was basically, “do whatever the hell you want.” So I started trolling the online dating sites.
I was honest about the situation I was in and I quickly discovered that the women whose profiles interested me were decidedly uninterested in guys still living with someone. At the time I couldn’t understand why, “trust me, we’re not really a couple anymore” just didn’t cut it. So my list of Qualities I’m looking for was basically reduced to “squats to pee”.
My first date in more then ten years was with a woman who described herself as ‘voluptuous’. Dictionary.com describes ‘voluptuous’ thusly: adjective 1.) having strong sexual appeal; 2. (of a woman’s body) having a large bosom and pleasing curves;
This woman did have a large bosom and she did have curves, but I think only a fetishist would have found them pleasing. She must have been close to 300 lbs (I’m not kidding).
The plan was dinner and a movie so we met at a restaurant close to the theatre and I was more then a little surprised when she arrived with her two daughters age 10 & 12. After we were seated, this woman suggested (read informed) that I pay for dinner for all of us and she would pay for the movie tickets. The girls were going to a kid movie and we would go to an adult movie.
Things started to go badly when the waiter came to take our drink order. They didn’t have the right type of cola and she tore a strip off him for that. The restaurant was featuring Cajun food that night so they had several ’blackened’ dinner specials. She apparently had never heard of this particular culinary motif. “Jezzus Christ, if I wanted my dinner blackened, I’d just get my daughters to cook it.”
The duration of the meal was spent with her loudly criticizing absolutely everything about the restaurant; the look of the place, the music that was playing, the smell of the restroom, the food, the staff, even snide comments about the other patrons. Meanwhile the two charming daughters grilled me about things I’m pretty certain had been previously suggested to them; how much I earned, how long I’d worked there, what my dad had done for a living, who I’d voted for in the last federal election, how many times had I been married, did the mother of my son know that I was out with their mother…
I should have just paid for my meal and got the hell out of Dodge, but I didn’t. I paid for everyone’s dinner and went with them to the theatre. As we were walking across the parking lot she informed me that she gets incredibly wet during sex and that she orgasms very easily. Then she thrust her ample chest in my direction and said, “These puppies are 100% natural.” Her daughters were very amused.
As I mentioned before, it had been a long time since I’d got laid and I remember that I wanted to see the movie so I decided to see it through to the end. We got into the theatre and the mother needed to use the washroom again and the daughters wanted to eat again. They were in front of me in the snack bar line when I looked over and saw a good friend of my soon to be ex’s. If she saw me with this woman she would call the soon to be ex to rat me out. Then she’d describe the woman I was out with and the soon to be ex would laugh at me and gloat. I could not stand the thought of that. So with the girls still in the line up and their mother still in the washroom I bolted.
Of course I couldn’t go home that early or else she’d know that the date was a bust, so I went to a neighbourhood pub to drink beer and feel very sorry for myself. And that was the worst date ever.
