May 6

The Widower and the Whore

After tons of email (130 at last count) and phone correspondence, I finally had a “date” with a music professor I met online. He was 38 and had the whole Moby thing going on—shaved head, big black glasses, unassuming demeanor. He'f lost his wife to cancer in January after a 10-year illness.

I was very excited to meet him, but the situation was so strange. We weren’t really supposed to date due to our circumstances. I mean he was ready to date and had been out with a couple women in the past month, but they weren’t right for him. I was way more right for him, but I was also a whore, and that wouldn’t work.

His house was charming and had arched doorways and slanty ceilings and was feminine, purple and green, packed with all his wife’s collections—little tea pots, picture frames, owls, Betty Boop, Halloween tchotchkes. I was amazed at how many ordinary things were purple—ear swabs, power strips, toilet brush, bubble wrap … He told me she would even PAINT things purple if they didn’t come that way. Some corners and shelves seemed like shrines, all these hanging delicate and sparkly decorations, whimsy occupying every square inch.

We spent hours in his dim living room talking about his wife’s cancer, how she got into the color purple after she got sick, how he lived in Singapore for three years, the dynamics of his family. He cried when he described his wife’s death, and I didn’t move to hug him—I didn’t want him to think it was an excuse to touch him. I felt very aware of the fact that I was a highly sexualized being and I didn’t want to make him uncomfortable.

He showed me all his instruments except "The One." He doesn’t believe in casual sex, can you believe it? He only wants to sleep with someone who is "Wife Potential," and has had very limited sexual experience, has never been able to fully explore sex the way he would like. It felt strange to be with someone who didn’t want to fuck me. I told him that and he said sincerely in his deep, sexy voice, “Oh I sure do, it’s just that I want more than that. I want to have an amazing sex life and go to music concerts and share everything else, and finally end up in rocking chairs, holding hands …”

Gulp. Kinda appealed to me.

He told me my blog didn’t intimidate him. You know, the one that has a slideshow of every pair of panties I own (70 and counting) and entries like:

***

I’ve Only Been Fisted Once

My friend, A., did the honors. Fisting is when a hand is inserted in the vagina. You work the hand in gradually, adding fingers one by one, until in goes the thumb and all you see is wrist. Final result is more like a Queen of England hand-wave than a balled-up fist. And having an orgasm that way is INTENSE. I’d love to try it again sometime, and of course I’d be willing to be the giver, too—I have small hands. But dunno if I can try doing it to a guy, as I’ve only gotten a finger up a guy’s ass, so far. I’m such a novice!

The best part: one time I sent my friend A. a new sexy pic of myself, and her reaction? A gloating, ‘I had my fist in that.’ ”

***

He read the entire thing, and fantasized about showing it to his future partner someday and discussing (and possibly trying out) the different post ideas with her. My blog opened up a whole new world of possibility to him.

After that night, things changed for me.

May 7

A professional client in his fifties hired me to go on a business trip with him. He instructed me to wear something very feminine for the plane ride and to be discreet.

I arrived at the airport wearing a pretty pink top and skirt, and we sat and chatted as we waited to board the plane. He was very excited to have me along. As we stood in line, he whispered pointedly, “Thank you for being discreet.”

I said, “Were you expecting me to jump up and down on your head?”

The funny thing is, as soon as we took our seats on the plane and got going, he started putting his hand up my skirt and my hand on his cock. GEEZ! I felt embarrassed for the woman sitting next to us, but figured we weren’t as obnoxious as the screaming baby three rows back.

He was like a kid in the candy store. We got to the hotel around 9 p.m. He didn’t even take me to dinner; just took me right up to the hotel room so he could have his way with me. He did. We had sex, and he came all over my belly, which with him means belly, tits, neck, hair and ears. He produces huge amounts of semen—WAY more than the allotted teaspoon. (I hear a pig produces a quart of semen per ejaculate...perhaps he’s part pig?)

Then I gave him a blowjob. (When he got close to cumming, he begged me to swallow it, but I didn’t. I spat it in the sink instead) and he requested that I wake him in the night with one as well. No problem, that’s my specialty. So I did, and afterward he murmured, “You are such a sweetheart.” Yeah, I know.

He woke up early to leave for his meetings for the day, and I left soon after to hang out with my girlfriend who lives in town. Yay, freedom! Kinda nice to start the day out with hundreds of dollars, then have time to yourself to eat sushi and drink sake and wander the cute shops, then have girl time with your friend where you drink more wine and then tea and swing on the swings at dusk until you feel like throwing up. Better than kinda nice, in fact. It was a great day.