His by Contract

by Ava Sinclair

  Camille tells me it would take a week to fully instruct me on how to ‘properly whore,’ but says the time we have should be enough to give me the basics. She asks if I’ve ever given a sensual massage, and I tell her no. She tells me that’s how she always opens sessions with new clients, and the best way to learn to give a massage is to get one. I hesitate. Is it allowed? Should I call Mr. M.? He said to put myself in her capable hands, so I decide to take him literally.

  We move to the bedroom, where I strip down to my underwear—powder blue push-up bra and white panties with powder blue trim—and lie face down on the bed. My heart quickens as I feel the mattress sag from Camille’s weight. I smell something—almond oil—and realize she’s rubbing it into her hands.

  Her touch is warm on my shoulders. Her voice is hypnotic as she kneads the muscles of my shoulders and glides her warm hands up and down my back. She’s telling me about the benefits of massage and she points out the pressure points on the spine, belly, and even the calf that she says will excite men when pressed. It’s an education, and I learn that she got a certification in massage therapy specifically for her job.

  I want to roll over, want to pull her into my arms and kiss that cotton candy pink mouth, but I lie there and remember that I’m just a client to her, a student she’s being paid to teach.

  After the massage, she shows me toys. She charges extra for using these, she says. She has anal beads and a tiny vibrating massager that fits on the fingertip—useful, she says, for stimulating the vas deferens and anus.

  I swear I’m not hinting for a demo when I ask her how much pressure should be applied, but when she offers to show me, I don’t object. Camille slides my legs apart and I stare at her hand. The little pink finger cot is covered with rubbery nodules. She turns it on and it whirs and disappears between my thighs. I come as soon as it touches my clit through my panties, but in truth, I’ve been on the edge since the massage.

  “You like that?” she asks.

  Oh, yes. I sure do like that. I miss girl time, and decide to drop some major hints to Mr. M. about how nice it would be to incorporate some into our life. But then I remember that it will be up to him so long as we are under the contract. What if he says no?

  “Are you listening?”

  I wasn’t. I look up apologetically. Camille is discussing lubes now. They’re not all created equal, according to Whore 101. She recommends Astroglide, and then a second product for use with sex toys since it’s easier on the latex.

  I could fill a notebook with what I’ve learned, and by the time it’s over, I want to feel like I’ve made a friend, but she’s all business as she packs up her small bag of things and looks at her watch.

  I stand up from the bed, my legs still shaky as I admire hers. “Did he… um… did he pay you?”

  She shakes her head. “He said to tell you the money is in his desk drawer.”

  “Right,” I say, surprised. “How much?”

  “Six,” she says.

  I excuse myself and find the money, which is in an envelope on his desk. Despite our arrangement, he’s gotten more and more casual with me. A couple of weeks back he had me come over to give him my opinion on new flooring for his office. Seriously. It felt weird, being asked to do something so domestic. And now I’m paying the woman he hired to give me whore lessons? On the way back, I stop in the hallway and take out an additional hundred from where my purse sits on the foyer table. I explain to Camille that it’s a tip.

  “That’s awfully generous,” she says. “Thank you.”

  I wonder if she has a family at home, someone to support.

  “It was well worth it.” I pause and tuck a strand of hair behind my ear and then cross my arms across the front of the robe I’ve donned over my underwear. “So… do you ever take new clients?”

  She looks up from where she’s tucking the money in her purse and gives me a smile.

  “This was a favor for a friend. I have all the work I can handle at the moment.”

  “Oh…” Disappointment is heavy in my voice and in my heart. I really like her, and would happily pay to get to know her better. Now I don’t even care that it’s not legal.

  “But situations change,” she said. “Your boyfriend knows how to reach me.”

  I watch her go and then walk to the window as the cab she’s hailing on the walk picks her up.

  I walk into the kitchen and open the fridge. I need something cool to drink. There’s a half a bottle of Evian. I take it out and put it on the counter and walk to the cabinet for a glass. I hear the whirring sound and see my phone lighting up. I forgot to take it off vibrate. I smile as I recognize Mr. M.’s number.

  “Hi,” I say.

  “Is this the escort service?” His tone is very formal. I set the glass down. I wasn’t expecting him to want to do this so soon.

  “Yes,” I say.

  “Good. I know this is short notice, but I’m in town on business and… well, I’m looking to have a little fun, relieve some stress. You come highly recommended.”

  My mind is racing. What would Camille say? “You’re in luck. I have an opening tonight.”

  “Hopefully more than one,” he quips.

  “First things first,” I say. “I assume the service informed you of the rates and rules? Two hundred dollars an hour, and we practice safe sex. If you’re expecting to ride bareback, you can go pick up a girl off the corner of Third and Vine.”

  I’m surprised at how easy this is, and how empowered I feel setting the limits. I expect him to laugh, to say we aren’t playing it like that. But instead he asks if I know where the Stonestreet Inn is located. I tell him of course I do. He asks if I can be there in an hour. I tell him that will be fine.

  I hang up the phone and pour the Evian into the glass.

  “Sometimes you’ll be my dirty girl,” he said. “My whore.” We’d written that into the rules.

  I drain my glass and head upstairs. Camille has blown my stereotypes right out of the water. I won’t be donning fishnets and crotchless panties. Instead, I change into an almost chaste beige bra and panty set and slip into a low-cut, drape-y wrap dress that I pair with impossibly high heels.

  I can’t help but smile as I realize that Camille left me an assortment of condoms on the bedside table. I throw them into my purse and glance at the clock. Stonestreet Inn is thirty minutes from Mr. M.’s condo, but it’s late, so I can make it in better time. As an afterthought, I pull our toy box out from under the bed and select something to make our evening more interesting.

  I take a taxi, just like Camille did. The Stonestreet Inn’s Georgian edifice looms over the cobblestone street. It’s in an older, wealthy part of town, and I must walk through a little wrought-iron gate and up an ivy-lined path to reach the steps. Inside, I tell the desk clerk I’m a guest, and give Mr. M.’s name. She rings a room and sends me up.

  I knock on the door of Room 4 softly. I’m a little nervous. Mr. M. opens the door. He’s freshly showered and has changed back into the clothes he’s worn to the gym.

  I hold out my hand. “Hi. I’m Sloane.”

  He takes it. “Sloane. That’s pretty. Come in.”

  I walk inside, and I turn and will myself to see my contractual lover as Camille saw him, to see him as I see my clients. I’m here to please, to do a good job. I’m not here to care, but he’ll be more pleased if I pretend.

  “You’re pretty,” he says.

  “Thanks,” I say, sitting down across from him. “So are you.”

  He laughs and rubs his hands together. “So… should I pay you now?”

  “After is fine,” I reply. “The dates are screened. We don’t entertain men who aren’t good for it.”

  I stand and untie the sash on my wrap dress, casually shrugging it off. Now I’m just in my bra and panties and heels. I toss the dress over the back of the chair and turn to him.

  “So, what would you like to do?”

  “Everything,” he said.

  “How about we star
t with a massage? Would you like that?”

  He doesn’t answer, but stands up, kicks off his shoes, and removes his clothing one piece at a time. Within moments he’s naked.

  “A massage sounds good for starters,” he says, lying on the bed.

  I picked up some baby oil before I left his place. I rub some in my hands as Camille did, warming it between my palms. I knead his muscles, knowing that my touch isn’t as practiced as hers, but he seems to like it. I work the knots out of his shoulders and move my hands up and down his back, pressing and pulling the ropy ridges of flesh. I find the spot along his spine between the third and fourth vertebrae, and a little to the left, and press. He gasps.

  “Whoa,” he says, looking back.

  “You like that?” I ask. “Good.”

  “Hey…” He turns over. “Enough with the rubdown. What else do you have?”

  “You’re paying for it. What do you want?”

  There’s a weird look in his eye, and I’m thinking maybe this isn’t as much fun as he thought it would be. It’s not as much fun for me, either.

  “Tell me what you want,” I say, and I can’t keep the sadness out of my voice.

  “I want to treat you like a whore,” he says. “A dirty whore.” He pauses. “Or I wanted to.”

  I stare at him, and I know what he’s thinking, because I’m thinking the same thing. Prostitutes sell access to their bodies for an allotted time. And in Mr. M.’s mind, and mine, it’s always seemed like something dirty, something taboo. For all his sexual experience, he’s never been with a prostitute. He’s probably never even met one until Camille. And my limited time with the pretty redhead made me rethink this game, this rule. Mr. M. can’t get into the game because the arrangement Camille makes with her clients is so close to what he and I have made. The only difference is that we do it every day, and I don’t charge him because I don’t need to do this to make money.

  “Oh, god, Sloane,” he says. “I’m sorry, but I think I may have fucked up when I made this rule.”

  I lie down beside him. “Don’t be,” I sigh, laying my head down on his chest, absently tracing his tattoo he never talks about. “Apologize to Camille. She’s the one who’s been misjudged. By both of us.”

  I sit up. “Did you know that you can give a blowjob through a condom that’s as good as one on a bare cock?”

  “Bullshit,” he says.

  I turn and lean over him to reach for my handbag and pull out a handful of condoms. I fan them out like a handful of cards. There’s a rainbow of colors and flavors—cinnamon sunset, orange burst, watermelon blast. I like watermelon so I choose that one.

  Mr. M already has an impressive erection, but the sound of the condom wrapper ripping obviously gives him a flashback to the days of less satisfied safe sex, because the fleshy rod starts to wilt before my eyes.

  “Don’t be like that,” I say, and reach in the purse for the toy I chose—a tiny vibrator called the Magic Bullet. I put it on the lowest setting and apply it as Camille instructed, running it ever so lightly along the underside of his cock and pressing it just under the head. Then I move my hand down and push the tiny vibrator against his taint. Now he’s back to rock hard, and I work the shaft a little before sliding the condom down over his cock.

  It looks hilarious, and a little uncomfortable. The condom is pink, with a little reservoir at the top; it looks like his cock has a little horn on it. I almost laugh, but I have something to prove. I lower my mouth onto his shaft. The claim of watermelon flavoring is a stretch. It’s more like berry with a hint of plastic. But I don’t care. I’m working the base of Mr. M.’s shaft as I draw his tightly clad head deep into my mouth. I’m generous with the spit, making his cock sloppy with it. But the moisture and the heat of my mouth is keeping him hard, and he’s moaning despite himself and driving his hips up off the bed to fuck my mouth.

  I’m loving it. I rarely get a chance to make him feel helpless. Tonight is my night. I surreptitiously stop and lick the little vibrator, which I push against his asshole as I return to sucking his cock. He’s fisting the covers and tries to rise, but I push my mouth down and push the little toy past his anal ring. I don’t push it in far, just far enough to nudge him over the edge. I can tell by the noise he’s making that he’s surprised. I feel the condom grow hot and stretch as his seed spurts into it. Normally I’d swallow, but now I just lean back and watch as he spurts, sending trapped jets of cum running down the sides of his cock to pool above the ring around the base of his shaft.

  “Well?” I say.

  He looks down at his cock like it’s betrayed him. Then he laughs and laughs.

  “You’re right,” he says. “I don’t want to start using condoms, but you’re right.”

  I lean over him. “That’ll be two hundred dollars,” I say.

  “What are you going to do with it?” he asks.

  I think for a moment, about how smart Camille looked in her cute retro dress.

  “Maybe I’ll buy myself a dress like the one Camille was wearing.” I reply with a wink.

  Chapter Nine

  Am I falling in love with him?

  That wasn’t the plan. Sure, we’re having sex. A lot of sex. A lot of toe-curling, mind-bending sex. But that was supposed to be what this was about. Sure, he wants to buy my clothes since the dress code is his idea, and he even insists on spoiling me because—according to him—he enjoys my company and our arrangement.

  But there’s been a shift in our interactions that I can’t deny no matter how hard I try. And since last week, since the evening with Camille that ended up with Mr. M. and me spending the night at the Stonestreet Inn, my feelings are more complicated. And the text I just got? I’m afraid it’s going to complicate things even further.

  It’s been a satisfying day for the most part, the kind that keeps me too occupied to think of anything but work. I had the pleasure of winning a case for a very nice lady I’ve been representing. Mrs. Brisby ran a music store with her partner for over thirty years, but he died last year. The pair was good at teaching piano and violin, but terrible at record keeping. So much of their partnership was by verbal agreement; they were best friends so there never seemed to be a reason to get lawyers involved. But then the partner’s son stepped forward and tried to claim the pair weren’t partners, but that Mrs. Brisby was an employee. He wanted the music school for himself, which he claimed was an inheritance.

  I don’t often get involved with clients, but in this case, I did. In fact, I spent six hours in a musty attic going through old records to reassemble the history of the school through receipts that showed Mrs. Brisby was the one who invested most of the money. Today we won the case hands down. Her partner’s son got a settlement, but the judge determined that Mrs. Brisby was the primary investor in the entire venture.

  Here I am, on cloud nine and feeling like a boss. And then I check my texts.

  I’ll be picking you up this afternoon. Don’t get on the school bus. I’m taking some time for us to spend together. Daddy.

  When we were negotiating the rules, the subtext was that each would be an extension of our agreed dominant-submissive dynamic. I wanted new experiences. I wanted to be brought to the edge, and I told myself this was about pushing my boundaries, about excitement. Some of the rules had given me pause. One was the punishment rule. And then there was this one. Sometimes, we agreed, he’d be my Daddy dom.

  I mentioned earlier that I have issues with the concept of punishment because of my mother. Well, I have daddy issues, too. Even now, memories of my father leave me with a sense of longing. It’s not a sexual longing, but a longing for the kind of paternal care and protection that I felt I was denied. My father had time for work and parties with my mother, but not much time for me. His expressions of pride and even love felt perfunctory. And when it came to my mother’s cruelty, he never intervened, no matter how bad it got. He was like Switzerland. Neutral. If we were in the living room and she started in on me, he’d rise and walk out without a
word. I’d hear the click of the door and realized he’d thrown me to the she-wolf once again.

  Neither of my parents believed in ‘spoiling’ me. I had to work for what I got, and sometimes things dangled in front of me didn’t materialize, like that bike. I was a tagalong, and I overheard my mother once tell an acquaintance that she never meant to get pregnant, but because they weren’t getting any younger they decided to go ahead and have me. They never really treated me as a child. I was treated more like a miniature adult born with tiny bootstraps I was supposed to use to pull myself up by time and time again.

  They sent me to a good college, at least. And it was there that I met Jeanette, an older student who became both a mother figure and my first female lover. She was the most nurturing person I’ve ever known, and I might have ended up with her except she was married with a family. Her husband, a jovial accountant, was either oblivious or complicit. I never could tell, because when she brought me around to dinner he was always very nice. Her youngest, a savvy high schooler, seemed quicker on the uptake and more perceptive. Her name was Lynn, and I will always think she knew something was up, but if she did, she never let on.

  Jeanette was optimistic and affirming. She gave me advice and baked me cookies and was the first person I told about my bisexual tendencies. She’d been around the block before with other women. She was a good lover, but she was a senior when I met her. The following year she graduated, her husband got transferred, and they moved. But she left me feeling like I’d finally known what it was like to have a mother figure.

  I still craved the missing paternal affection, however. I just wasn’t sure how I felt about ageplay. Would it, like the spanking, be an emotional awakening in which I found comfort in something that had always felt negative? I wasn’t sure, even as I agreed to it in our negotiations. Now I’m wondering how this may impact my growing feelings for Mr. M.

  I should have suspected today would be different when he offered me a ride to work. I usually drive, but Mr. M. insisted. We spent last night at his house and this morning he had my clothes laid out for me. I keep several business suits at his house for when I sleep over. He had new underwear, plain white and cotton. In retrospect, that should have been a clue.