As a phone sex operator, my name was Cherry, and I loved my regulars.
I had the wanna-be tranny, Miss S. Satin, who by day was a high-profile psychologist in a major metropolitan city (I wouldn’t want to be too specific, as she may be reading; we developed a friendship that extended beyond the phone.), and by night was a tortured soul in the suburbs, wearing the yoke of a bullshit marriage, instead of the cashmere sweater-dresses and knee-high Italian leather boots of which she dreamed of openly coveting. There was no graphic sex involved in her fantasies, it was mostly just domme girl-talk. I believe that the time I spent on the phone with her, which was always multiple hour stretches, is what led me to believe that what I was doing actually had some therapeutic benefit for the customers. I don’t think that’s entirely incorrect, either. But I do realize now that if you work with that altruistic attitude on your sleeve, it will be recognized and taken advantage of by even the sweetest of regular customer. One must never forget that everyone wants to get the most for their money, and in a business where so many lines are inconsistent and undefined, what the customer gets for the money he paid is always a game of tug-of-war.
There was Mark, who loved black women, and since Doreen hadn’t had any working on the day he first called, I was given the task of being not Cherry, but Cherita, a sassy mocha-skinned sexpot, who got into all sorts of sticky situations that allowed him to play the role of my savior. His favorite was when I’d get my toe stuck in the bathtub faucet during a bubble bath, and he, as my apartment superintendent, would hear my cries and come dislodge my toe, saving the day. Naturally, I’d be so grateful for his help, that I’d fuck him with wild African abandon, as a thank-you. Nevermind the fact that my “black woman” voice is about as convincing as Ann Coulter’s.
With phone sex, it isn’t about accuracy, it’s about enthusiasm.
That’s why Rick loved me. He liked to talk to Cherry, his teenage daughter who loved black men (seriously, there were a lot of customers that had race involved in their fantasties) and rebelling against her preacher daddy. I would take my boyfriend, whom he named “Malcom X” (Yes. He. Did.) into the church, and fuck him on the altar. The blasphemous banging would be SO hot, that it would bring to life the hanging statue of crucified Jesus, who would then pry himself free of his cross and join in the fun. Now, of course, Jesus doesn’t join a party without inviting his unlikely friend, the devil to take a turn as well. I spent countless afternoons squealing “Fuck me, Satan Daddy!” loudly enough for my neighbors to notice.
It takes A LOT to shake me from my comfort zone. It isn’t impossible though, and the few things that will achieve that are what ultimately cost me my sweet little side job. You see, Doreen was an animal lover, rescuing and fostering dogs, so she would not, under any circumstances, allow bestiality calls (I learned this after doing one, and requesting to not do any more.). However, she had no problem with the societal subset that she referred to as “Chesters”. As in Chester the Molester, an adorable term for monstrous men, who felt no compunction about describing, in vivid detail, all the things they loved about children. I tried to justify these calls as a healthier outlet for the illegal and illicit urges of men who knew the difference between right and wrong. I tried to convince myself that it was a radical coping mechanism, keeping real children safe from the beast that lurks within, but I always knew that was bullshit. Those calls drove me to tears every time, and eventually drove me away entirely. You’ve probably heard someone say, at some point, “there are things you see, that you can’t un-see” usually by some douchebag, hyperbolizing the trauma he suffered by seeing a fat woman in a thong bikini. Well, it also rings true that there are things you hear, that you can never un-hear, and the disembodied voices of the men who I had to doubt were just describing sick fantasies, were the gold watch I took with me when I retired. Because it’s true, that there really is no such thing as a free lunch.
After that, waiting tables wasn’t a punishment. Once I’d heard a man breathlessly describe his preschool dream date, bringing some bitch (You know the one, and you know she’ll find a reason not to tip.) extra lemons for her water didn’t seem so bad.