Working Sex (16 page)
Authors: Annie Oakley
Imagine, now, that you are me. You live on the ground floor in a neighborhood where Cubs fans and frat guys parade around, frequenting the Irish pubs, the Mardi Gras-themed sports bar next door, and occasionally the palm reader upstairs. You live alone and barely pay rent on your freezing-cold roach-hole apartment by working five nights a week taking calls. You are in a relationship with a female-bodied genderqueer who you call your boyfriend. You have phone sex with men in the pantry while your lover watches TV and listens to your fake orgasms. The work suits you especially in the winter because the cold makes your back hurt and it’s better not to have to leave the house.
“Ohhhh,” Jimmy gurgles. “I’m getting fucked.” He sucks in air through his teeth and whimpers. I can’t remember the last time I had actual sex with my lover. My disability has been particularly disabling lately, and the phone sex has driven a bit of a wedge.
“You’re pathetic,” I tell him.
“I’m sorry mommy. I know, I’m a pathetic faggot,” Jimmy’s voice is little.
“That’s right, you’re a dirty, pathetic faggot,” I parrot. He enjoys this technique—repeating key phrases back and
forth. I listen to him grunt as he gets pounded and I get a clear picture. I know what he’s doing.
forth. I listen to him grunt as he gets pounded and I get a clear picture. I know what he’s doing.
“Boris is about to cum, mommy,” he tells me.
“I knew it, you fucking pervert,” I say. Boris is Mistress Tabitha’s dog. A Great Dane.
The next line is unwritten. There is no summing up, no justification, no one true feeling about the experience of listening to a man get fucked by a dog. Understand me. When you are on a phone-sex call you are experiencing it, you are complicit. You can laugh about it later, but during the call it’s a reality. If you were me, by now you would have listened, dozens of times, to this man stroke, suck, and get fucked by this Great Dane. You would have encouraged him, degraded him, rode through it with him. The first time I experienced this, I felt like something in me was fundamentally changed. I didn’t stop it. I couldn’t. I didn’t want to.
A memory came back to me, of a dream I had when I was thirteen. A dog with a boner. It built up and built up until he came with a bright shower of color, leaving me with the feeling of shame and release. My friend and I would always tell our dreams to each other on the walk to school. That day I was embarrassed. I hemmed and hawed and when I finally told her she looked at me like I was gross and said, “That’s it”?
The dog cums. That’s it. Shoots a load of jizz up Jimmy’s
ass. I listen to Jimmy groan and take it, then slide off to suck the cum off the dog’s cock as it softens.
ass. I listen to Jimmy groan and take it, then slide off to suck the cum off the dog’s cock as it softens.
“Oh, mommy it’s so good. It tastes so good. It’s sweeter and more liquidy than a man’s cum.” No. Don’t want to know. Shut off. It’s just words. Blah blah blah. La la la. Jimmy gives Boris a Milk-Bone and says “good boy,” then decides to climb onto the giant dildo he has suctioned to his yoga ball. I think this is a great idea and go “boing, boing” with him as he rides his bouncy ball, telling me stories about a conference he went to recently with Mistress Tabitha where they did a demonstration with Boris. He is particularly proud because he won the Biggest Slut trophy for getting fucked by every man (and dog) there.
If you are a phone-sex operator reading this you may be thinking to yourself, This is all in this guy’s head. And that’s what I thought at first. But over time I came to see the difference between the men with hyperactively surreal fantasy lives and Jimmy, who I believe actually did at least 90 percent of what he talked about. Rather than grasping for stereotypes and glamorizations, as many men do, I feel Jimmy was reaching for every real experience that he could possibly pull into his fantasy. He wants everyone, everything involved in his sex life.
“Oh, mommy, is Stacy there?” Jimmy begs. Stacy is the name I gave to my lover after the time I told Jimmy my boyfriend was there. But when he heard the voice in the background
he said, “That sounds like a girl.” Ever since he has begged to talk to Stacy.
he said, “That sounds like a girl.” Ever since he has begged to talk to Stacy.
“Yeah, she’s here,” I say. “Stacy, Jimmy wants to talk to you.”
“Tell him I think he’s a dirty faggot,” my boyfriend calls and Jimmy groans.
He insists on talking to her and I ask how much it’s worth to him. He promises me a thirty-dollar tip and I get “Stacy” on the phone long enough to spit a couple of awkward half-hearted insults at him. The phone is handed back to me and Jimmy is ecstatic.
“Oh mommy that was so hot,” I can tell he’s getting closer. “Oh mommy, talk in that baby voice, please, mommy,” I can hear the ball squeaking in the background.
“Dat’s a good widdo baybee,” I say.
“Oh, I love you mommy,” he coos.
“Good widdo baybee, good boy,” I say.
“I love you mommy.”
“I love you baby.”
“I love you mommy.”
“I love you baby.”
A friend once asked me “Is that okay for you?” when I said that I sometimes tell clients I love them. It’s not hard for me. I don’t even feel like I’m lying. Doesn’t mean I have any intention of taking the relationship further.
But I guess you could say that Jimmy and I took it further. It just happened naturally. One night, while he recounted the exploits of his weekend, I said, “You use condoms, right?” His voice changed then, and he said he did, usually, probably not as much as he should. “It’s important, Jimmy. You need to be safe.” I didn’t know how this would go over. I don’t usually interject wake-up calls into phone-sex sessions. But after that night he would often refer to it, telling me, “and I made them use condoms, and I thought about you, and it made me feel so good that you cared.”
Not everything about him was quite so sweet and tender. My boundaries were pushed, often, like the period when he was always shoving a snake up his ass. A real live snake with slithery skin and a flicking forked tongue. I said, “Isn’t that suffocating the snake?” and he said, “No, they go in holes naturally, they burrow.” I went along with it and listened to him take fifteen inches, groaning as it wriggled into him. I drew the line at him fucking the dog. I said, “It’s one thing to let it fuck you, but a dog can’t consent to you fucking it.” He seemed to get the point, though he argued a little, but ultimately he didn’t do it, at least not on the phone with me. He was as desperate for my approval as he was for my disdain, so he would apologize profusely every time he knew he crossed a line.
So after a year and a half of talking to him a few times
a week, as weird and deep and twisted and real as the connection was, he just felt like a normal part of my life. Not taking up any more energy than he was paying for, and giving me good stories for later. My relationship with my lover ended and I got into another one with a trans man who would sometimes get on the phone and be Jimmy’s daddy. Jimmy paid $50 for that. I’d go on tour and come back and Jimmy would always call within a couple of days, saying, “I missed you mommy.” Sometimes he would disappear for a few weeks and then reemerge with more crazy stories and new fetishes being explored. One time he told me he had taken to shoving a cucumber up his ass and going to the mall with it inside him. “I saw two people I knew,” he told me, groaning with the memory, “and I talked to them. It was so hot.” I wondered what those people thought of the interaction.
a week, as weird and deep and twisted and real as the connection was, he just felt like a normal part of my life. Not taking up any more energy than he was paying for, and giving me good stories for later. My relationship with my lover ended and I got into another one with a trans man who would sometimes get on the phone and be Jimmy’s daddy. Jimmy paid $50 for that. I’d go on tour and come back and Jimmy would always call within a couple of days, saying, “I missed you mommy.” Sometimes he would disappear for a few weeks and then reemerge with more crazy stories and new fetishes being explored. One time he told me he had taken to shoving a cucumber up his ass and going to the mall with it inside him. “I saw two people I knew,” he told me, groaning with the memory, “and I talked to them. It was so hot.” I wondered what those people thought of the interaction.
He was insatiable. There was no endpoint, he was in constant expansion. He attended frequent sex gatherings where he was always the star, dressed up in his wigs, heels and hose, thigh-high boots and lipstick. He even managed to get action as a regular suit-wearing dude staying at hotels on business trips; I loved his story about the knock-knock game that preceded a porn-watching and blow-job fest with the businessman in the room next to his. One particularly tender moment happened on Christmas night, when I got to inaugurate his new Real Doll, by naming it Trent and
making him say “I love you Trent” while he fucked its tight rubber hole. I marveled at the breadth of his vision and the depth of his appetite. I loved him for living it, for doing what felt good, as much as I was taken aback by the scope of his entitlement, access, and compartmentalization. I bet he’s a very good businessman.
making him say “I love you Trent” while he fucked its tight rubber hole. I marveled at the breadth of his vision and the depth of his appetite. I loved him for living it, for doing what felt good, as much as I was taken aback by the scope of his entitlement, access, and compartmentalization. I bet he’s a very good businessman.
At a certain point that winter, I started to get really burnt-out on phone sex. I was sad that my relationship wasn’t working and that I had more intimacy with random dudes than I did with my long-distance lover. I was grossed out to have their issues occupying space in my precious new studio apartment. And I was pissed off that I had to struggle so fucking hard to claim my sexuality, when these men have the resources to occupy other people’s space with their unexamined shit. I couldn’t help feeling invaded with every call, and my cute, sweet, friendly persona became more bitter and monotone.
Nights passed without intrigue while Jimmy found new outlets. A kinky new couple who he played with. They met over the Internet, then at a local café and went back to their place together, where he fucked the husband and the wife fucked him. “Uhhh, mommy, it was so hot,” he gurgles at me. I stare blankly at the computer screen, click click click, playing solitaire. “Wow.”
“Oh and mommy, I told them about Boris, and she wants to try it, wouldn’t that be hot mommy?”
“Mm-hmm.” Click click.
“Wouldn’t that be hot, to watch Boris fuck her pussy?” I can hear his hand slapping his cock. Another childhood memory comes back to me. I’m ten years old at my dad’s softball practice in the park. I’m petting this big white fluffy dog who knocks me over and keeps jumping up on top of me. It’s freaking me out, and my dad and all his friends are laughing so hard it takes them forever to pull him off of me. “What was he doing?” I ask. “He was trying to hump you.” I hide my face from all the laughing men. Any one of them could be Jimmy.
“You make me sick,” I tell him.
“I’m sorry mommy,” he says, groaning as he cums.
And then I didn’t hear from him for a while. I’d sign on every night expecting his call, but nothing. Just a bunch of giantess fetishists and CBT enthusiasts, pedophiles and crossdressers. Weeks went by. I was glad that Jimmy wasn’t calling. I didn’t have the energy to act like I cared what he was doing or make him feel loved.
i
have to pause and ask you Jimmy. how are you, now? do you feel loved? is it forgotten? are you fixated? haunted? healed? you know that this is the part of the story that ties the knot. a part of me is true to you always.
have to pause and ask you Jimmy. how are you, now? do you feel loved? is it forgotten? are you fixated? haunted? healed? you know that this is the part of the story that ties the knot. a part of me is true to you always.
i
’m in the middle of making dinner the next time Jimmy calls. “What are you doing mommy?” he asks, hearing the chop chop of the knife. I start talking about how I’m cutting vegetables so I can boil him in a pot of soup like Bugs Bunny. He doesn’t totally go for it but he’s not put off. “I missed you mommy.”
’m in the middle of making dinner the next time Jimmy calls. “What are you doing mommy?” he asks, hearing the chop chop of the knife. I start talking about how I’m cutting vegetables so I can boil him in a pot of soup like Bugs Bunny. He doesn’t totally go for it but he’s not put off. “I missed you mommy.”
“I missed you too,” I say, deadpan. Then, to be nice, “Where have you been?”
“Something bad happened, and I had to take a break.”
I stop my chopping. “I’m sorry,” I tell him, seriously, leaving open space in case he wants to say more.
“You remember that couple I was playing with?” I say yes. “Well I went over one day, and they tied me up, and a bunch of their friends came over, and it wasn’t play. . . . It was like they were mad at me.”
They kept him tied up for ten hours. He was repeatedly raped and beaten by the couple and five of their friends. When they finally let him leave he was bruised and bleeding and almost unconscious. He hadn’t told his roommate or mistress about the couple, so nobody knew where he was. Oh Jimmy. Poor baby. I hope he can hear the genuine compassion in my voice when I tell him how horrible that sounds.
I have no training in dealing with this. One time a
nineteen-year-old with a developmental disability called me and basically reported a trauma that was happening to him in his home. He hung up the second I said it was wrong for his parents to do that to him. I agonized over that choice afterwards—was it just his fantasy? Was I shaming him?—it seemed so real.
nineteen-year-old with a developmental disability called me and basically reported a trauma that was happening to him in his home. He hung up the second I said it was wrong for his parents to do that to him. I agonized over that choice afterwards—was it just his fantasy? Was I shaming him?—it seemed so real.
In this case I can tell this is not Jimmy’s fantasy. He’s confiding in me, as someone he trusts. I wonder what it will be like to go back to phone sex with him again after this conversation. He says his mistresses have been really nice to him while he recovered, and he just went to his first sex party again a couple nights ago.
“There was a head mistress, the lady who owned the house, and I got locked in a cage with her eighteen-year-old daughter,” he says, with that telltale gurgle. I brace myself. I don’t like this eighteen-year-old-daughter-in-a-cage situation. La la la. “We could barely move, the cage was so small, we could just wiggle around, and they made me fuck her,” slap slap slap.
“Oh, that sounds hot,” I’m not totally lying. Despite or maybe because of the creep-out factor, it is a hot story.
“It was so hot,” he growls. “I fucked the shit out of her.”
“Yeah?”
“I fucked her and fucked her, I fucked her raw, I made her scream . . . ”
I go along with his story. His voice sounds different, there’s another layer to it that wasn’t there before. Then it softens. He wants to be humiliated. I can’t do it with the fervor I used to. I feel sad and tender towards him. I talk about sucking his cock, one of my favorite phone-sex activities, something we never really do together, and he cums and says he’ll call me again soon. I think that was the last time we talked.
i
don’t really even expect you to remember me. it’s been eight months and you’re a busy guy. you’ve probably had at least a couple new better mommies who only know the now-jimmy, not the then-jimmy. it’s okay. i hope you never read this. but somehow, magically, i hope you know it. you have a witness.
don’t really even expect you to remember me. it’s been eight months and you’re a busy guy. you’ve probably had at least a couple new better mommies who only know the now-jimmy, not the then-jimmy. it’s okay. i hope you never read this. but somehow, magically, i hope you know it. you have a witness.
love,
mommy katie
golden
Ariel Smith
I
am standing
strong, fresh, and golden
in the day glow softness
of the kiddie stroll
tight skin
bathed in the sickly, soothing yellow of streetlights
we’re all here
scrubbed shiny
made up like perfect, pretty dollies
I be chapped lips and fishnets
am standing
strong, fresh, and golden
in the day glow softness
of the kiddie stroll
tight skin
bathed in the sickly, soothing yellow of streetlights
we’re all here
scrubbed shiny
made up like perfect, pretty dollies
I be chapped lips and fishnets
pinkie toes swollen and sore from digging into the edges
of these high heeled boots
$49.95 at the store down on Hastings
god I hate these fucking shoes
don’t like feeling all wobbly and unsure when I walk
like some little girlie playing dress up
wanna feel big and swollen inside myself
sexy, dangerous monster
huge powerful strides
glowing self confident
then
familiar sound
car tires cut slick through pools of oily water
slowly, slowing
take your pick
there’s so many lined up
pink, powdery candies
waiting to be drawn into the warm danger of your
moving vehicle
leaving you with traces of our sugary sweetness
I lean over
big, shiny smile wasted on you
my long hair brushing against cold metal of your
window frame
“how old are you baby?”
“thirteen, fourteen?”
“i’m how ever old you want me to be”
“$60 for the best head of your life”
these words fall from my dry, painted lips and then
laid before you
my words small poems laid before you
on cold, cracked cement
eye contact
drawn in by my prototypical innocence
car door swings open and tonight fear rushes
tonight fear rushes all hot and demanding like
a fever
biting at my ankles like a bad dream
but I step over it
on it
crush it, crush it
put all the weight in my twelve-year-old body
on that fear and crush it
slide in beside you your warm hand on my thigh
talking all light and empty like Styrofoam
crumbling
we pull way and that fear is left dishevelled
beside my six
with just traces
of pink, sugar sweet, powder.
of these high heeled boots
$49.95 at the store down on Hastings
god I hate these fucking shoes
don’t like feeling all wobbly and unsure when I walk
like some little girlie playing dress up
wanna feel big and swollen inside myself
sexy, dangerous monster
huge powerful strides
glowing self confident
then
familiar sound
car tires cut slick through pools of oily water
slowly, slowing
take your pick
there’s so many lined up
pink, powdery candies
waiting to be drawn into the warm danger of your
moving vehicle
leaving you with traces of our sugary sweetness
I lean over
big, shiny smile wasted on you
my long hair brushing against cold metal of your
window frame
“how old are you baby?”
“thirteen, fourteen?”
“i’m how ever old you want me to be”
“$60 for the best head of your life”
these words fall from my dry, painted lips and then
laid before you
my words small poems laid before you
on cold, cracked cement
eye contact
drawn in by my prototypical innocence
car door swings open and tonight fear rushes
tonight fear rushes all hot and demanding like
a fever
biting at my ankles like a bad dream
but I step over it
on it
crush it, crush it
put all the weight in my twelve-year-old body
on that fear and crush it
slide in beside you your warm hand on my thigh
talking all light and empty like Styrofoam
crumbling
we pull way and that fear is left dishevelled
beside my six
with just traces
of pink, sugar sweet, powder.
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