People never know what kind of mischief awaits them until it's already upon them, and that was the tagline for my life. Somehow, I was living large, but not all that in charge. How long could it last?
As crazy as the stories I will share sound, I can assure you that they are all true. Only the names are changed to protect people's privacy and dignity.
Have you ever met someone so unbelievably hot that you'd do anything to go out with them? The answer to your question is a big yes. The story I'm telling you happened during a time of self-discovery and slightly before the internet wound up in everyone's pocket.
In 97, I was about to completely lose my mind as I found myself chasing after a woman that didn't make sense. She was older, edgier, smarter, and sexier than any woman my age. Twenty-year age differences don't matter when women defy the ravages of time.
Susanne looked like she was barely thirty. She had a body that was more believably manufactured than worked on. She stood a whopping 5'1", had blonde hair that she wore in a cute and curly style, eyes as green as emeralds, and a tan from top to bottom. With an incredible ass put together from years of squats and 34 D-Cup boobs that on her tiny frame were impossible not to notice, it was amazing she was single.
Sue being single was by choice. She was independently wealthy, a businesswoman, and she had "special" tastes as she described them. One of those tastes was young men, at the time, specifically me.
I'm David, by the way, and at the time I was barely 25. I stood nearly 6'4'' tall, weighed about 220, and was muscularly built, with brown hair, brown eyes, and the start of a bodybuilder's body.
I met Sue while surveying a prospective client. We hit it off because she had an attitude that was playful but feisty. After hinting at things for a couple of months, Sue finally hit me with a dinner invitation. I was excited.
Dinner was at her place, a large one-story a few miles from town. She didn't do it justice. The place was fabulous. She was sitting on enough space to have built three or four houses. The driveway from the road to her house was at least a half mile long.
After Sue showed me around, we ate dinner and she opened up a nice bottle of wine. We each had a glass before she asked if I'd like to sit on the porch with her. As she swayed by me, another bottle and her glass in hand, I eagerly followed.
"So, what do you think of me' casa?" she asked.
Looking around, it was gorgeous. She was a lucky woman. I asked how she came into such luck and she told me that she'd been aggressive with some investments, had a couple of start-ups, and didn't need to work at Hinkley's but enjoyed the work.
"So how is it that such a successful, beautiful, intelligent woman is single?"
Sue smiled, "That's the million dollar question."
"Well," I asked her. "Want to let me in on the secret?"
Sue told me that most men find her crazy, and the rest couldn't keep up with her or her particular tastes and quirks. Men her age were either too uptight, slowing down, or weren't playful anymore.
"Oh, come on," I laughed. "You can't be that rough on the fellows."
"I can be demanding, a little domineering even, but life's short so why not be me?"
I saw her point. Sue was being Sue, and the rest of the world be dammed if they didn't like it that way. It did make me curious, what sort of things had scared other men away.
"So, what did you do to run the rest of the boys off?"
Sue smiled, putting a finger between her teeth. She was pondering something mischievous, and that was fine. I could handle anything, or so I told myself.
"I don't know if I should tell you," she smiled. "You might get spooked."
"Nothing shocks me," I lied. Some things shock me, and some would over the next several years. That's a different story. When I said the words, Sue sat up straight, put her wine glass on the small table between us, and asked...
"What if I told you that I want to see that bod of yours, right now?"
"Really, that scared off other guys, you telling them what you think?"
She giggled. "No, hun, I actually wanted them to strip for me, right then and there. They wouldn't play along."
"Huh, I wonder why?"
"It's not like there was that much of a chance of getting arrested or in trouble. It was mostly for fun, to excite things."
"I still don't think I'd get scared off," I told her, admittedly intrigued by what she'd said.
"O.K., then do it."
Why, I didn't know, other than it sounded sexy. But without hesitation, I stood up, kicked off my shoes, took off my polo shirt, and slid my jeans down. When I folded them up and put them on a ledge, Sue looked disappointed.
Looking around, there was no risk unless someone came flying up the driveway at warp speed. What the hell, I thought as I put my thumbs inside the waistband and pulled my boxers down to my ankles.
"Oooh, you are a good boy!" she exclaimed, a big smile on her face as she clapped. "Will you stay that way for me?"
"You mean, for the rest of our date?"
"Yes, silly, for the rest of our date."
So, I did. I stayed nude while finishing our date, which lasted well into the morning. Sue showed me the rest of her place, which included a wide open space before the fence line. She insisted on holding hands as we walked around the grounds, occasionally clinging tightly to me. It was weird at first, but after a while, I began to get comfortable this way.
"So, in my dream fantasy, I have made a ton of money, have an incredible place, my own businesses, and there's just one thing missing," she told me.
"What's that?"
"This, everyday."
"I suppose I could be convinced to come stroll around here holding hands with you everyday," I told her, hoping she was going to help take care of the raging erection she'd caused.
"What if I invited you to stay here, in this incredible place with me, but there was a catch," she asked.
"Um, what about a second date?"
"Why bother waiting, I've had my eye on you for two months, and so far, you're the first guy not to freak out when I tell you what I want," she admitted.
"What's the catch?" I asked her.
"Three things. One, you don't try to change or judge me. Two, I'm going to be the Games Master, and you have to play my games. Three, whenever you are home, you're going to be restricted to wearing shoes or sandals, and nothing else," she explained.
"Alright," I wondered, "What's in it for me, besides you?"
"I will introduce you to a life you can't imagine, fantasies you've never known you had,,and pleasures beyond belief. All you have to do is say yes," she told me, slipping the little black dress off her shoulders as she stood in front of me.
My new life started with a yes and the most fantastic blowjob. From there on out, I was the center of her attention. It wasn't all about her, however. She did cater to my fantasies, and in ways that I wouldn't have thought possible.
One fantasy in particular, having always been a bit of an exhibitionist, was to be naked in front of strangers. I'd told her that I'd fantasized about being a nude servant at someone's house. We'd toyed with the possibilities, but there was part of me that admitted it would be exciting to do it for someone I didn't know, like a novelty business.
"Oooh, I love it when you're a bad boy," she gleefully responded with an excited smile.
It was about six months into my new life when she mentioned my fantasy again. I was surprised when she brought it up, and equally surprised when she told me it might be possible.
"I mentioned it to a friend of mine, and after showing some pictures of you, the opportunity is there for the taking if you're really game."
"Hell yes," I told her, a surge of excitement traveling through my body.
"Good," she said. "So, here's what I've arranged."
The next day I had to wear sandals, a pair of gym or running shorts, and a tee shirt. When it was time to leave, Sue told me she had some shopping to do and was going to have lunch with a friend in a town about an hour from home. She explained that she'd be dropping me off and there'd be a note at the front door when we got there. She said if I was game, all I had to do was follow the instructions on the note and I would enjoy five or so hours of fun like I had never imagined.
I was a bundle of nerves and excited energy the entire way there, particularly as Sue would occasionally reach over and rub my crotch. When we got to the house I was nervous as it was on a moderately busy street at noon on a Sunday. The houses were very close together judging by the sides and the front. I sat there in the car, pumping up my courage to go for it, when Sue said, "Come on, don't chicken out. I didn't chicken out when you dared me to get crazy with that stripper a couple of months ago."
"You're right," I told her. "And I've thought about doing this for a long time."
"Exactly," she smiled.
I got out and nervously walked the twenty or so feet to the front steps. When I got to the door it was just like she had said. There was a note with my name on it.
Unfolding the note, I read it to myself. Holy crap, I thought. It read:
"David, before you press the button or knock, I want you to to take the brown paper bag off the chair to your side, remove your clothing, and give it to Sue. Then you may come back to the door and ring the bell."
I looked at Sue who had a mischievous grin on her face. She yelled, "Don't be shy now."
Looking around and examining the area, I opened the bag, removed my shirt, and put it inside. I checked the area again, not wanting to get into trouble for what was a little harmless fun, and slipped my shorts off. I put them into the bag and hustled them down to Sue's Mustang.
"Have fun big guy," she laughed as she pulled away.
