Black Book Diary Entry: Barbara

Black Book Diary Entry

I met Barbara Online on one of those dating sites, Cupid or something. I was drawn to her by her correspondence. She was one of the few women who was skilled enough with the English language to keep me interested and it always excited me when I saw I had an e-mail from her.

I had no idea what she looked like. In the age of the Internet, she could have been a man for all I knew. Except, I thought of her as being short, pear shaped, and having gray hair for some reason. I'm not sure why, maybe because she told me she was an accountant, a controller for a company and that's what I imagined a female controller, one more interested in numbers than romance, should look like.

After corresponding with her for a few weeks, I cajoled her into sending me a photo of herself. I had already sent her one of me. With her knowing what I looked like, I felt encouraged that she was still interested in continuing a dialogue, which was a good thing. Certainly, I'm not a bad looking man, but you just don't know if there's still going to be a connection, once you know what the person on the other end looks like.

Finally, she sent me the photo. It had been taken by her daughter and she was standing a distance away from Barbara. It wasn't a very well constructed photo, but it was good enough for me to tell that she was a very attractive woman. Only, I didn't know how attractive she was, until I met her in person, some months later.

I was going through a separation, after a long and fairly happy marriage. My wife and I were friends more than we were lovers and once the kids left the house, the quiet was too much to bear. Still, the marriage endured long enough for us to have two children, raise them, and send them off to college, before she had become attracted to a co-worker. At the time I thought it was a blessing in disguise. Now, that I know what I know, my life had suddenly become a tragic mistake.

I remember the first time I met Barbara. She was so nervous and I was so excited. It was a little bit of a drive to meet her, with her living more than 100 miles from me, at the time. Still, I was willing to make the drive for the chance of meeting my pen pal with the hope that it would develop from a correspondence to a romance.

I had packed a small bag with a change of clothes, in case my car broke down and I needed to stay at a motel or, my real reason, if I got lucky enough for her to invite me to stay overnight. Fortunately, it was the latter rather than the former. We hit it off immediately. Yeah, I got lucky and she invited me to stay.

It was a spring day in late May and we spent the afternoon going for a walk, after I took her to lunch. We walked through a picturesque park that had a path leading down to a river. We were content enough there to sit on a fallen tree and continue our getting to know one another dialogue, where our e-mails had left off, with face to face conversation.

It was there that I kissed her for the first time. Never had I been with a woman so small. She was 5'5" tall and weighed a miniscule 115 pounds. I've always been with a fuller figure woman. My wife was a plus size woman and a woman that I met, when I was first separated from my wife was certainly not as heavy as my wife, but she wasn't as thin as Barbara was either.

Barbara was thin, but not unhealthy thin. She was still very curvaceous. It sounds like an oxymoron to be thin and still be curvaceous, but she was. She said her nickname in high school was the body. Proportionally put together, she was very symmetrical and had a nice womanly muscular tone to her body. Her claim to fame was her great ass, so round and so firm. To be honest, she did have a nice ass.

I seem to have a thing for women from the United Kingdom, my first love, Aileen was Irish and my wife, Arlene, was Irish/Italian. Some of the most beautiful women in the world are from across the pond. Barbara was no exception, her family heralded from Scotland and Ireland.

I have a thing for freckles and Barbara had them. Every woman I've ever been with has had freckles. Maybe it has something to do with having a Howdy Doody doll when I was a kid or enjoying reading Alfred E. Newman's exploits in Mad Magazine. Only, unless Bill Gates gave me a billion dollars, I don't think I'd be sexually attracted to him. Mr. Gates has freckles. I should qualify that I'm only attracted to freckles when they are on women.

It was a memorable day that I spent with Barbara that first day we met and she asked me to spend the night. After having a light dinner that she made, we sat on the couch and made out like two horny teenagers. It had been a long time since I had made out like that, the last time was with Cathy when I was helping her to babysit, eons ago, and again when I was dating and romancing my girlfriend, who became my wife.

Never have I been as excited as I was that evening sitting on the couch making out with Barbara. I had rounded all the bases quickly and was headed for home, my first hitting an in the park homerun, a grand slam. Then, when she unzipped me, pulled out my cock and started blowing me, while I fondled her perfect tits, I was in Heaven.

I couldn't believe it. I never had a woman be so aggressive. Maybe because we were both older. Why waste time playing games? If you like someone, show them that you like them. In my case, I'd send flowers. In Barbara's case, she gave me a blowjob. Hey, it worked for me.

Never in my life have I received a better blowjob. I've been blown by lots of women, but this was different. Either she was highly skilled at it and had sucked a lot of cocks, or she knew what she was doing. Maybe she read up on how to give a blowjob, in Blowjob for Dummies. Yet, whatever it was, it was great and it didn't take me long to reach the point of wanting to cum in her mouth.

I couldn't believe it. When I was about to cum, when I asked her to stop, she invited me up to her bedroom to continue our love connection. I couldn't wait to make love to her.

Talk about a romantic evening, I saw stars. I couldn't stop kissing the woman. I even thought about a possible second marriage, eventually, if everything worked out as well as this first night was going. She was an amazing woman and I was so very attracted to her.

"Before we do this," she said. "I need to tell you something."

Oh, oh. I figured she was going to tell me that I needed to wear a condom or worse that she had some kind of sexually transmitted disease. Only, what she said was worse than that to me, a heterosexual man, who had spent most of his adult life married with children.

What did I really know about the world in the way it is today? I couldn't help but feel, suddenly, that I was in the movie, A World According To Garp, starring Robin Williams as Garp, when he was looking up at a house he was considering buying and it was suddenly hit by a plane.

"We'll take the house. Honey, the chances of another plane hitting this house are astronomical. It's been pre-disastered. We're going to be safe here."

"What is it," I said to Barbara. "I have broad shoulders. There's no problem too big that we can't get around."

"I used to have a penis. I used to be a man," she blurted.

At first I thought I misheard her. Then, I thought, for sure, that she was joking. A man? Her? Look at her. Look at her ass?

"What? A penis? Used to be a man? What do you mean?"

Never having been a big fan of Jerry Springer, I didn't know that Barbara was once Barry, a post-op transsexual.

"Oh, look at the time," I said looking at my watch. "I need to start heading home. Thank you for a lovely evening. I'll be in touch. Bye."

I always wondered what happened to Barbara, if she ever found Mr. Right, as I sure to God was Mr. Wrong.