I met Bailey in 1997, she was the manager of a very posh, high-end gym. She was the embodiment of sex. She exuded sensuousness, sensuosity. I don’t know the proper word. She dressed very casually. Regular old Levis jeans or loose cargo shorts, and a T-shirt. Nothing fancy. So it wasn’t her clothing. She didn’t speak of things sexual, she wasn’t lewd. It was probably her outward confidence that people found so attractive….sexy. She left a trail of hardons in her wake.

I know lots of women that don’t fit the societal norms of what is considered beautiful, yet they leave you with a stiff dick just talking to them. All of those women have one thing in common…self-confidence.

Unfortunately for many guys that knew and wanted Bailey, you needed at least one of two things to get into her pants. You needed to have a big thick cock or a big thick wallet. Preferably both. I had neither.

I guess the proper, though crass, definition would be ‘Gold Digger’, and or “Size Queen.”

With me, she’d be happy to sit on the couch, kiss, and have me go down on her, but then she’d give me some religious bullshite about why she couldn’t sleep with me.

Her gods were the almighty ten-incher and hundred-dollar bill.

Because of her need for cock size and gifts, the men that she dated were usually high-power, married men. Men that she’d met at the gym. It’s difficult to hide a big dick when you’re wearing a speedo in the pool or hot tub. She had full access to those areas, so it was easy for her to peruse the genitalia.

She loved the gifts….jewelry, clothing, rent being paid, car payments, and she always raved about really big cocks. Big, as in, more than nine inches long and at least two inches wide. At a whopping six inches on my best day, that left me high and dry.

These men were high-power guys that made their fortunes by being ruthless pricks. They basically took what they wanted without regard for anyone’s feelings or well-being. That included her pussy.

It didn’t matter to them if she wasn’t in the mood, or didn’t feel well. Put out, or I’ll give the gifts to someone that will. Because of this, she didn’t trust any of them. I don’t think she trusted anyone at all.

In her world, people gave specifically to get. She didn’t know anyone that gave for the sake of giving, at least she wouldn’t be able to recognize it if she encountered one.

I’m one of those people that gives for the sake of giving, not for the benefits reaped. That’s not a boast, it’s just a product of my upbringing. I was taught to lift people up. To give to people that couldn’t necessarily give back.

One by-product of her distrust was that she couldn’t achieve orgasms by anyone but herself. She’d told me that the 'boyfriend du jour' would get her close, but she would have to rub her clit to take her over the edge.

Those guys didn’t give a shit. They paid, they came, and they went home to their wives and families. Even the few times that I went down on her, she had to finish the job with her fingers. Didn't do much for my ego.

Back to the men in her life.

As I stated previously, her ‘gentlemen’ friends were married, so they couldn’t include her in their lives. She knew better than to cause trouble for them because she’d end up in a dumpster or trauma unit. Tony Soprano-type personalities. This left her a lonely person. Wanted by all, cared for by none. Well, one...myself, but I didn't really count.

Christmas 1999.

She called me on Christmas Eve, in tears. “Can I come to your house tonight? I’m all alone. I don’t want to be alone on Christmas.” Obviously, all of her ‘gentlemen friends’ were with their wives and children. They didn’t even cast a glance or thought in her direction.

I told her to come over. I wanted to tell her that the reason she was alone was because of the company she kept. That would have to wait. After all, it was Christmas.

I shared my Christmas dinner with her and we retired to the living room to watch the Yule log on tv and drink some homemade eggnog. She was a lightweight drinker, so after a few egg nogs, her inhibitions dropped. So did her pants.

I was very surprised. “Wait, Bailey, you’ve always given me multiple reasons why you won’t sleep with me and now you’re pulling me to the bedroom. Care to explain?”

She told me she’d explain later, so off to my bedroom we went.

I like lots of foreplay, so I went on the growl. Much to my shock, she came without rubbing herself off. It shocked her as well.

“You made me come! You made me come! Nobody has ever made me come! I’ve always had to rub my clit while they fucked me!”

I told her that it happened because she let her guard down.

The alcohol helped but she thought it was because deep down inside, she trusted me. She finally realized that I was the only person in her life that had ever given to her without any thought of getting something in return. It took the wine to bring forth the truth. In vino veritas.

We kept my bed busy for the rest of Christmas Eve. She had many splendid orgasms, courtesy of...you guessed it, me. She never had to touch herself that night. We woke around 9 am to a snowy Christmas morning. All in all a postcard-perfect Christmas.

We sat in front of the tree and discussed what had happened the night before. She said, “Those guys don’t give a shit about me, they only want some pussy or a blowjob. I’m nothing but a whore to them.”

I couldn’t disagree. She asked me to tell her why they treated her like that. Oh boy, she's not gonna like this one bit.

I held her hands and said, “I'm going to be blunt. You sort of got what you asked for. You set your sights on powerful, wealthy, or well-endowed men that have families. They’re not gonna let you be a part of their lives, so did you really expect to be treated otherwise by them? They use people and throw them away when they’ve gotten what they want. They get their rocks off and walk away, leaving jewelry or a check on your nightstand. Unfortunately, to them, you’re nothing more than a safe piece of pussy.”

The truth can be a painful, brutal wake-up call. This one hurt like hell. She cried for the better part of ten minutes. I held her and let her cry it all out.

Her biggest problem was that she couldn’t make it on her own, or at least she didn’t think she could. She took the time to examine her life and her way of doing things. She made list upon list of things that had to change and had me read them so as to give an opinion. I don’t give advice. I’m not an expert in anything. In the end, she went back to school and got a degree in business. She found a great job in California. Her new job pays for all of the things she needs in life.

I don’t know if she stopped dating that type of ‘gentleman’. Hopefully, she left their kind far behind. I lost contact with her when she moved away.

I hope that she’s been able to find someone she can trust and love. Very few days pass that I don't think of her. I still miss her. I hope she’s happy.