Surprising Sex Issue That Shouldn't Exist


I did not expect that.

For a moment I didn't answer. I made a confused face. Then, at realizing Olive couldn't see my face, I realized I had to answer. Not bombard her with more questions.

"Mostly like a release. On a big scale. Imagine feeling very tense and then being able to suddenly let go of all that tension, specifically in your groin area. And the feeling of easing spreads throughout your body, like you're un-tensing other muscles. You feel happy, calm and energized at the same time. It's great."

"Shit," Olive said.

We spent the next hour talking about her lack of sexual conquests, nights that didn't work out as intended, bad ex-boyfriends and the fact that she never tried self-pleasuring herself because throughout adolescence, college apartment-sharing days and moving back home after being unable to find a job, she had felt someone was always around, ready to bust her at any moment so she couldn't relax. And her embarrassment was greater than her desire to try. Damn you recession, the depths of your reach are immense.

Now, I felt the need to step in: "This is something you learn to do, not expect to surprisingly happen. Everyone is different, so thinking the next person you sleep with will be able to guess exactly what you like will not happen. You need to tell him, or at least encourage when he's in the right direction. Think of yourself as a cheerleader, not a coach."

Olive was silent. But I knew she was listening. Maybe she was impressed I made a sports analogy.

"I think you need to figure out what you like on your own, first. Do not get paranoid. Lock your bedroom door, put some furniture in front of it, whatever. I think it will help ... do you understand the general idea of it?"

Olive snorted, "Yes, I think I know how to do that. I just get nervous about my fucking family running around without boundaries."

"I laughed. "Ok, maybe you should get yourself some help ... of the battery operated variety?"

Olive laughed, "If you can't come right out and say it, how are you going to help me?" (the range of my word prudeness is vast, and most of my friends know and make fun of me for it. Bastards)

"A vibrator. Go buy one. You don't even have to do it in person. Go to and order one, to come to your house, in discrete packaging, and then figure it out. Some woman can be very picky. Try different positions, fantasize, don't give up because it's taking awhile. And don't put it on the highest speed because you think that will work the fastest -- you will vibrate your clit off."

Olive didn't respond but I heard the distinct tapping of fingers on a keyboard ...

"I'm not going to push you on the oral sex part. I do think you should give it a try and maybe your apprehension has more to do with the last man you slept with rather than the act itself. It's not meant to be a dominating act or something dirty or demeaning. Be open-minded, because it's something that will benefit you."


"Promise you'll try this?" I asked.

"Yes. I don't want to wake up 30 years old and realize I've never had an orgasm."

"Good. You'll be happy you tried. Call me if you have questions." I said. After a few more minutes of small talk and goodbyes, we hung up for the night.

That conversation happened over three weeks ago. Since Olive is single, I wasn't going to follow up with her about the oral sex at all, but I was of course curious about her progress on the personal front. As I was debating whether to text her or not, I received an incoming message.

" :) Yippie. Luv u"

That was enough of an answer for me. Kudos, Olive. Welcome to the big leagues (I'm on a sports roll).

Readers... anyone else know someone like this? This conversation seriously through me for a loop -- I didn't know sex-guilt or awkwardness was so pronounced in today's oversexed culture. Who's got a story to tell?

Invest in Batteries,

Lady J

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