Little Charlotte was eighteen months when this happened. We'd been using Whitney, a sweet little girl from the inner city, to babysit for over a year and she was maturing into a lovely young lady late in her junior year of high school.
So it came as a bit of a surprise when, as we left for a play, she asked, "Is it OK if I have a friend over after Charlotte goes to sleep. ... To, uh, work on homework together?"
I looked over at Jesse. "Male or female," I asked.
"Well, it's my boyfriend, Ethan."
Jesse and I looked back and forth at each other. "You're not going to get pregnant, here, are you?" I asked, surprising myself how quickly I got to what was bubbling below the surface in my mind.
"Oh no, Mrs. Westmore, no. We're not having sex," she replied quickly, as if I would have been surprised or judgmental if they were. I just wasn't sure about it happening in our living room.
Jesse looked at me and shrugged.
I shrugged back. At least it was safe here.
"I suppose," I finally relented with Jesse's consent.
It was a few minutes into our usual departure instructions, that another thought came to mind. "Uh, Whitney, look. No alcohol, no drugs. We can go to jail if we give you alcohol, or your mother smells it on your breath, and we could lose our house if we have drugs here," I cautioned. Not that there hadn't been drugs here before, at least marijuana, before Jesse's employer stared testing.
"Oh no, Mrs. Westmore, never."
I wasn't sure how confident I should be, but the die was cast. I gave the same warning to Ethan, the first time I saw him.
A couple weeks later, Whitney was going to sit while I went to a meeting. Jesse was out of town. "So how is it going with Ethan?" I asked. "Are you two making out here ... when you're not doing your homework?" I added with a wink.
The girl turned red with embarrassment, but eventually came clean. "Uh, well, yes."
Not surprised, I followed up with, "So how far is it going?"
"I let him play with my breasts," she confessed.
"And?"
"Oh Mrs. Westmore, he puts his hand in my panties."
"And?"
"Oh God. He lets me rub his, you know, thing."
"And what happens when you do that?" as if I needed to ask.
Long pause.
Looking down at her tennis shoes, "It… squirts," she mumbled barely audible.
I realized I was giving her the 5th degree. "I'm sorry, Whitney, for asking so many questions. I was a teenager too, once," remembering what happened at a much earlier age to me, and being shipped off to the east coast for an abortion. "It's just I want you to be safe."
Then, after a long pause, I opened a drawer under the TV. "Look here," I pointed to a box of Trojans, "I know you're not having intercourse yet, ... but if it ever comes to that, I want you to know these are here. I had to have an abortion when I was your age, and I still lie awake at night wondering about who I killed." I had told Jesse I'd bought the condoms, so he wouldn't suspect anything, but not the abortion.
"Oh Mrs. Westmore, I'm so sorry."
Every time we had Whitney babysit and she had Ethan over, I checked the box afterward. It remained unopened, though that didn't prove anything. And sometimes, when Jesse drove her home, how do I say this, it seemed like it took a bit too long for him to get back.
"She sure has a lot of questions," I reported to him, edging into the concern I had.
"Yeah, she was asking what it is like for a man, and like when was my first time, and all that," he laughed.
Mollified, with a few doubts lingering in the background, I added, "She told me Ethan is finger fucking her. And she likes it a lot." Jesse grabbed me and started tearing off my clothes. Finger fucking was just the start of our frolicking. "What did you tell her," I asked as he came up from between my legs and his cock found its way into my vagina.
"I told her it's wonderful," as his thrusts grew stronger.
So one night, Jesse was away. I had some sort of event, I can't even remember what, but it was cancelled at the last minute. I called Whitney and told her. I was still breast feeding my Charlotte and let her suckle for a good half hour. I'm not sure who liked that more, me or her. I'm one of those lucky women that gets a little orgasm from that. I had just changed her diaper and put her to sleep when the doorbell rang. I was surprised it was Ethan.
"Ethan!"
"Oh! Mrs. Westmore! Is, uh, Whitney here?"
"No, I had to cancel. Didn't she call you?"
He pulled out his phone. There was a missed call and a voice mail. "Oh. Something went wrong. I didn't hear it!"
"Well, come on in anyway," I suggested, "Would you like a pepsi or something?" I did want to talk to him in any case.
"Uh, sure, Mrs. Westmore, that would be nice."
I went to the kitchen and brought him a coke and a glass of wine for me. "Sorry I can't give this to you, Ethan."
"Thank you. That's OK."
We sat on the chaise longue sipping our drinks. "Can I ask you something, Ethan?"
"OK?"
"How's it going with Whitney?"
"What do you mean?"
"Well, have you two, you know, had sex? Intercourse?"
"No," a long pause, "Mrs. Westmore, it's just, well, you know, we just use our hands and stuff."
"She jerks you off?" Of course I knew.
"Yeah."
"And you finger her pussy?"
"Yeah."
"But you two haven't had intercourse?"
"No. She says she's not ready."
"Well. Aren't you the gentleman for respecting that," I offered, "but you must have had sex with somebody?"
"No. Nobody.
"But you want to, right?"
"Oh yes, I can't wait, Mrs. Westmore."
A naughty thought was building in my head. I asked him a few more questions. "Is Whitney the only girl you have, you know, played with like that?"
"Yeah, and I've never really had sex either."
I looked him straight in the eyes. "We could do something about that," I said.