At age 27, I found myself in a situation that mortified me, and which turned me on precisely because it was so embarrassing. It involved my getting spanked by a young woman; and I emphasize "young," in that she was 18. She was my landlady's babysitter and house-sitter.
I lived in an apartment in a townhouse, and I worked in advertising. I was single and hadn't had a girlfriend in months. I was horny, and my submissive streak was increasingly evident in the fantasies I'd seek out online.
Nelly, my landlady, lived in an apartment that took up the first two floors as well as the basement. Then on the third floor were two small apartments: the one I rented, and another rented by a 40-something woman named Ellen, who was often away on business.
Nelly had recently turned 40, and she had a nine-year-old son, Chad, who lived with her most of the time. Chad was away every other weekend or so with his father, Nelly's ex-husband, Bill, who'd moved out a few months after I'd moved in, two years earlier. Nelly had hired Diana to watch Chad some afternoons and evenings, usually two or three times a week. This had started even before the separation, when Diana was a junior in high school. Diana had recently started college, and she still lived with her parents, a few blocks away.
One autumn Saturday evening, I was walking into the townhouse just as Diana was about to leave. I'd had a quiet, and lonely, evening by myself, browsing in a bookstore and getting a quick dinner in its coffee bar. It was about 9 p.m., and I'd seen Nelly arrive ahead of me from down the block. She was probably now getting Chad ready for bed.
Her apartment door was open, and Diana walked out. She was wearing a short skirt, as she often did. I had to force myself not to look down at her legs. We said hi, and then I turned to open my mailbox.
I'd met Diana several times, and we'd had some brief conversations, but I didn't know her well. I wasn't sure how old she was. I thought 18, but I wanted confirmation of that, as my tendency to surreptitiously ogle her made me wonder. She was a gorgeous blonde, who'd been a cheerleader and swimmer at high school, and was likely to continue one or both of those in college.
She lingered in the hallway, eyeing me. "Chad was a real brat tonight," she said.
"Oh really?" I replied, trying not to sound like the word "brat" piqued my interest.
"One of these days I'm going to give him a good spanking," she said, cheerfully.
Now I was really trying to be nonchalant. I looked at my mail, then glanced over at her. She was watching me closely. I averted my eyes and started to turn toward the stairs. I felt I was blushing.
"I might give you one too, Roy," she said with a laugh. "I bet it would do you some good."
I gave her a quick glance with a half-smile. "I better go," I mumbled.
As I started to walk up the stairs, she waved her hand toward my butt, making a pantomime of a smack.
"Definitely would!" she said exuberantly.
She gave another laugh as I walked up the stairs.
I let myself into my apartment, then looked in the bathroom mirror and saw that I was blushing deeply. Then I dropped my pants and underwear, sat on the toilet, and jacked off. I had to try hard not to groan when I came, as I was afraid Diana might still be at the bottom of the stairs and would hear me.
Diana was frequently on my mind the next few days. When I ran into Nelly as I got home from work on Monday, I asked how babysitting was going.
"Fine," she said. "Diana's no-nonsense. She's going to house-sit for me this weekend. I'm taking Chad apple-picking, and we'll stay at a B-and-B."
"Sounds good," I said. Eager to turn the conversation back to Diana, I said, "Oh, and yes, she's clearly very responsible. How old is she?"
"She just turned 18," Neely said, starting to chortle. "Too young for you, mister!"
"Of course," I replied, with a slight scoff. I walked upstairs, went to the bathroom, and jacked off again, thinking about Diana in a cheerleader outfit, holding a sorority paddle. This time I couldn't stop myself from moaning loudly.
When I got home from work on Tuesday, Nelly's door opened as I was getting the mail. It was Diana. She was wearing jeans this time, which I saw as I tried to look casually, glancing downward in her direction.
"Been behaving yourself, Roy?" she said, smirking.
"Yes," I said quietly.
"Yes, ma'am," she corrected me.
Thoughts raced through my mind. Part of me wanted to say, "I'm almost 10 years older than you. Show some respect for your elders, young missy!"
Instead, I gave her an awkward glance and then looked down at her jeans. There was a moment of silence.
"Well?" she said, in a challenging tone.
"Yes, ma'am," I said.
"Good boy," she said. "I'll expect to see you at 6 p.m. on Saturday. I'll be house-sitting, and there'll be plenty to do."
