Sedulous Sugarbaby

A girl's gotta do what a girl's gotta do...

Transcript: Some people are just lucky. Born with a silver spoon or gifted with winning a genetic lottery, they barely have to ask to get whatever they want. I on the other hand have had to work my ass off for whatever I got.

Paying for school is expensive enough. Tack on the added cost of basic living expenses and that leaves little extra, usually none, for anything else, including clothes, especially when you’re trying to maintain two separate wardrobes. I should explain. To put it simply, I’m a crossdresser. I enjoy getting glamorously dolled up from time to time and prowling the night as my female alter-ego, Daniella. Over the years, I’ve gotten pretty good at it too. I even have my own pair of deceptively realistic self-adhesive silicone breasts. Most of the guys I meet have no clue what I really am. It’s all good fun, but Daniella was always only a money sink until I met Harry.

Another regular at a nightclub I often frequented, our arrangement began the night I, in an attempt to ward of Harry’s advances, began ranting to him about my financial woes. Don’t get me wrong, I usually enjoy getting hit on, I just wasn’t in the mood that night for empty sweet talk and cheesy pickup lines. One look at the suave, over-confident youngster being fawned over by a dozen half-clothed tramps and comfortably dressed in a slick Forzieri shirt and Edward Green shoes, and I took an immediate disliking to him. Harry had the air or a rich, arrogant, and rude playboy about him, the combination of which being something I abhorred. I wasn’t that far off either, so I paid him little attention until he proposed. 

No, not marriage. Turns out he knew about me, and I mean really knew about me, and had a thing for pretty little traps like yours truly. He offered to be my sugar daddy, paying for everything: tuition and rent for starters—flashy dresses, cheeky skirts, and to-die-for shoes, the finest cosmetics, scintillating lingerie, diamonds, pearls, and whatever else my little heart desired. All for a small little price. How could I say no?

I handed him a wish list that night of all the things I could think of at the moment. At the top? Lube, and plenty of it. Like I said, I work my ass off for what I have.