Between the ages of 16 and 24, I worked in a pizza place as a delivery driver. The best thing about the place was the steady stream of attractive waitresses, hostess, and occasionally managers that would come in. I had my share of fun tie-ups there, but I may as well start with the first.
Mary was a girl I had gone to school with since the 7th grade; a petite, short blonde about 5'3" tall with something of a baby face and green eyes. One evening when I was in the back scraping gunk from the dishes, she opened the back door, stepped out and lit a cigarette (all of our waitresses and managers smoked, and bullshitting with me was the only other thing to do while they did it). She began picking on me about something from earlier in the evening (unfortunately, I can't recall what it was); she'd say something to me, I'd come back with a ludicrous threat. Rinse, lather repeat.
Eventually in response to some insult, I sighed "Jesus, if you don't shut up I'm gonna duct tape you to the light pole out there." "Go right ahead; I'd just get out of it anyway." "And how would you know that?" I asked, sensing an opening. "I grew up with two older brothers who would always tie me up, I got really good at getting out of it" she answered, taking a drag. This was the best opening I was ever likely to get. "I bet you five American dollars that if I tied you up you could not escape." "You're on" she said.
I washed my hands as she finished smoking, and our shift manager wandered back. He decided to come on out and watch after I informed him of our bet. Then I went out to my car.
I drove something of a beater back then, so carrying rope and duct tape in the trunk was sort of a practical matter and thus didn't raise many eyebrows. I returned to where she was waiting, the black roll of duct tape concealed in my pocket and 6 feet of rope in my hand. When I got there, she held two fists together in front of her. "Uh uh; other way"...without missing a beat she turned around and crossed her wrists behind her.
I began looping the rope around her wrists, trying to hide visible excitement (no kidding, my hands were shaking a bit; I hadn't tied a girl up since I was 9). I realized that I had a little too much rope for her small wrists to make it tight enough. I did the best I could and knotted it off.
She turned around and began to struggle a little bit. "Stop, don't start yet" I said, and she silently stopped. I removed the tape from my pocket and ripped off a fairly long strip, a little bit amazed that she didn't protest or raise an eyebrow at this wholly unnecessary step. She kept her lips together as I put the tape across them, stretching from one ear to the other before smoothing it down and desperately hoping I didn't appear too exciting as my fingers traced the contour of her lips and cheeks under the tape. "OK, now you can go" I said.
She didn't even struggle at first; instead she worked her jaw muscles and lips until she was able to begin pulling the tape into her mouth and between her teeth. She kept chewing at it until it only stuck at one corner of her mouth. Only after the gag was gone did she begin trying to untie her hands.
First she moved her bound wrists up to the middle of her back and then down. I couldn't easily see what she was trying to do, but I didn't care. I just enjoyed watching the struggle. But then disappointment struck; after about two minutes of unhurried and methodical working of the ropes, she put her hands out in front of her, ropes still dangling loosely from one wrist. "Okay, best two out of three; we'll tie you to the chair in the office". "Not gonna bet on that, haven't been tied up in a chair yet."
'Yet' she said. Oh ho ho. The shift manager called from his vantage point "Betcha I can do better." "Nope, no way, no military knots" she answered (said manager was an Air Force NCO in his forties who worked with us part time).
I never got a chance to tie her up again, sadly. But I would get the chance to tie another 3 co-workers over the next few years and gag two more than that. I can tell you those stories too if you're interested, but first let me tell you what the best part was:
The best part is, I never did pay her the five dollars.