I met Bailey in 1985, 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.

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 descriptions would be ‘Gold Digger’, and or “Size queen.”

With me, she’d be happy to sit on the couch and kiss, receive oral, but then she’d give me some religious nonsense 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 six inches, 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, didn’t feel well ... put out or I’ll find someone that will. Because of this, she didn’t trust any of them. I don’t think she trusted anyone at all. She thought that people gave to get. She didn’t know anyone that gave for the sake of giving ... at least she couldn’t recognize it if she encountered it.

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.

Bailey hadn’t met many people like that in her life so that probably made recognizing it all the more difficult.

One by-product of her distrust was that she couldn’t achieve orgasms by anyone but herself. She’d told me that they 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, 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.

Back to the men in her life. As I stated previously, her ‘gentlemen’ friends were married, and 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 1996. 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.