18. Oliver
Oliver
Idon’t have to wait long.
She’s got her hair half down today, a glittering barrette pinning it back. I’m looking forward to watching her try to get it back to some semblance of order after I’ve made her fall apart.
“Hello,” I say, remembering the moment when she called me ‘sir’ in that sing-song voice.
I want that again, desperately. But it’s a line I haven’t crossed with an escort before. That kind of title, that kind of control isn’t appropriate for this type of relationship. It’s too intimate, too deep.
“Hi,” she murmurs back.
“Lock the door, please.”
She dutifully goes to do so and turns back, leaning against it, awkward and unsure.
“Go ahead and pick another one,” I say, having carefully removed the two dildos she’s already used.
They’re slowly getting larger in size each day, and it gives me a perverse rush to see her looking along the line of them. I know she’ll pick the smallest, but I love that she’s playing the game at all.
Walking along the shelves, she doesn’t make a sound. When she reaches the final shelf, she turns to me, her eyes shining as she indicates the toy she wants. It’s not the smallest, I was wrong, but it’s still a lot smaller than my cock.
“Take off your clothes, Lissa.”
As always, she fidgets at the command, but complies after a few seconds of hesitation.
I adore watching her get naked. It’s in no way a show; she does it practically and logically, as if she’s solving a puzzle in her head.
Other escorts have enjoyed showing off for me. They’ve every reason to, their bodies were beautiful. But Lissa does it as if against her will.
I frown at that thought.
“Are you uncomfortable?” The words fall out of my mouth before I can think them through, and she pauses, standing in her underwear, glancing up at me with wide, worried eyes. I curse inwardly.
“You haven’t done anything wrong, Lissa. But you don’t look as if you like this part.”
Her hands drop in front of her, looking down at her clothes almost longingly. She clears her throat.
“You don’t take your clothes off and…” she says in a small voice as my gut clenches. “I don’t mind, but I don’t…”
“Don’t what?”
She shrugs. “I don’t like my body.”
For a long time, I can’t speak, astounded by her confession. That it should come from an escort is surprising enough, but from such a gloriously beautiful woman is mind-blowing.
“Why not?” I ask, my voice hoarse.
“I… I just never have.” She bites her lip, scratching awkwardly at her arm. “Sorry. I suppose that’s not something you want to hear.”
“Lissa, I want to hear how you’re feeling, that’s why I asked. And I‘ve been around enough women to know that what I say won’t change your opinion of yourself, but you’re very, very beautiful. I hope one day you’ll see that.”
Those long lashes hover over her eyes, her fingers still scratching at her arm, and I have an idea. Walking to the drawer, I pull out the shirt she didn’t wear the day before and take it over to her. She frowns at it as I hold it out.
“Put this on, if you like. You can cover yourself up if you want.”
“N—no, that’s alright?—”
“I want you to be comfortable.”
After a little pause, she takes the shirt and pulls it over her shoulders. It looks like a bathrobe against her tiny body, but there’s something incredibly sexy about her standing there in my clothes.
“Sit on the chair,” I say, moving to the back of the room to grab the toy, then returning to place it on the desk beside me.
Lissa is sitting rigidly straight in the chair, tense and anxious.
“How are you feeling?” I ask, pulling out my phone and sending a calming playlist to the speaker at the edge of the room. I hardly ever play music while I’m working, but as the soft strains of a harp play, I can see Lissa begin to relax.
“You know,” I say conversationally without giving her a chance to answer. “We don’t have to do anything today if you’d prefer not to.”
“No, I want to,” she says quickly, and her cheeks flush. I nod, ridiculously pleased that she’s so eager.
“Alright, well, why don’t you tell me what you want to do?”
“Do you ever take your clothes off?” she asks. “I mean, for sex?” A flash of irritation whips through me, but the innocent curiosity in her eyes makes me pause.
“Not usually, no,” I reply flatly, waiting for her to ask me why, like they all do.
“That’s important, then. I don’t want you to do anything you’re not comfortable with either.”
I stare at her. The weight of her words hangs between us as I process them. I’m so used to taking care of my partners, I’ve never had anyone say that to me. It loosens some tension I was carrying deep in my body.
“Thank you,” I say softly. “I appreciate that.”
I watch her silently for another minute, listening to the ticking clock on the wall, and then she stands up, removes the shirt, her bra and her panties, and sits back down in the chair stark naked, looking determined.
“I feel better now,” she says timidly.
“Good. If it helps, I adore your body. I’d love to have you naked in that chair all day just to look at you.”
Her cheeks are so pink, and I feel a little guilty for making her self-conscious, but it’s the truth.
“Are you ready?” I ask.
“Yes,” she replies breathlessly. Her eyes are fixed on the dildo beside me, and I pick it up, pulling the small tub of lube from my pocket and covering it in a thin layer. Lissa watches me, her hands subconsciously moving closer to her gorgeous pussy.
I walk over, holding it out to her, as she takes it gingerly, like it’s a bomb.
“I want you to push it inside you today,” I say, and I feel my cock twitch in my pants. “I want to watch you pleasure yourself with it, but don’t come. The only way you’ll come today is with my cock inside you.”
She makes a little gasping moan at the back of her throat, and her pupils darken as she takes the toy out of my hand.
I walk back to the desk and lean against it again, waiting for her to start.
After a moment, she lowers it between her legs, her thighs spreading wide. My cock is so hard I can barely stand to be separated from her, but the way her body trembles takes my breath away.
She places the toy at the entrance of her body, her eyes focused on it as she slowly begins to push it inside.
She’s not even trying to be erotic, and it’s driving me fucking nuts.
Slowly, it slides all the way in, then she pulls it out, her thighs widening further as her toned stomach punches upward, a low moan breaking free.
As she starts to thrust it back and forth inside her, her moans grow in volume. They’re still quiet, but filled with a longing that makes my dick ache.
Still watching her, I walk over to the drawers again, open the top one, and take out a long piece of fabric.
I walk over to her, holding it in my hand as she watches me, a curious look on her face. I go behind her, lowering the fabric over her face, and then slide it into her mouth.
“Bite down on it,” I say, and she does without question. “You need to be quiet, and this is your reminder. If you need things to stop, place your hands on the cushion beneath you.”
I tie it at the back of her head, then slide my hands over her shoulders and down to her breasts as she continues pleasuring herself.
Remembering how much she liked it the other day, I pinch both her nipples without warning, and she bites down hard on the gag, groaning deep and guttural as I release them and come around to stand in front of her.
Slowly, I unbuckle my belt, open my pants, and pull out my cock. Her eyes zero in on it, and the sight of her with the toy inside her body, and the gag in her mouth, makes pre-cum burst from the tip.
“Are you ready for my cock?” I ask, as her hand falls away from the toy and she leans back in the chair. She hasn’t pulled it out, leaving me to do that, and she hisses as I yank the thing free. I love the way she grips the arms of the chair so tightly her knuckles turn white.
I roll a condom over my dick, as she sits there waiting for me.
“The chair or the chaise?”
Her eyes flicker to the chaise, and I can tell that’s what she prefers.
Without warning, I lift her up and walk over to the chaise. I kick the cushion off it, lay her down, and push her legs apart.
I can read her pleasure more clearly now, and I know she’s desperate for me, her breath coming hard and fast.
“Are you ready for me, Lissa?”
She mumbles something that sounds like a tortured yes.
“I should make you wait all night. Deprive you of it for as long as I can. But I can’t wait any more. I need to feel you around my cock.”
Then I tug her down the chaise, lining us up as she pants beneath me, my cock rubbing against her entrance, and then I push inside with one long, perfect thrust.
Her hands grip my shoulders, breasts arching toward me as I suck at them, as I shove my cock into her.
Her mouth opens on a silent scream, the gag falling away as she writhes beneath me.
“Don’t. Make. A Sound.” I say and then begin to fuck her harder. She collapses back against the curve of the chaise, legs wide apart and wrapped around me as I piston my hips back and forth, the tight heat around my dick so fucking addictive.
It’s perfect, unexpected, and so good I find myself on the edge in minutes. Usually, my partners have commented on my stamina, on how long I can fuck a woman before I come, sometimes giving her the chance for two orgasms before I’ve even finished.
But today, it’s nothing like that. I’m fighting to hold off right from the start. The image of her sitting there, all pale innocence, fucking herself with the toy has me completely undone.
“I want you to come on my cock,” I murmur into her ear. “Come for me, Lissa.”
I push my cock into her brutally hard, and she lets out a scream that I have to muffle with my palm as my orgasm hits me like a freight train.
I collapse against her, panting heavily.
I’ve never lost it that fast in my life.
Lissa’s body is languid beneath me as I pull back, looking down at her clear, dewy skin and beautiful eyes. She’s so fucking stunning.
Slowly, I pull away, wincing as her body tries to suck me back in, feeling wobbly as I stand. My pants have pooled around my feet, and I kick them away, my legs bare, but my shirt and tie are still on.
“Fuck, that was good,” I say. “Sorry, I usually last a little longer than that. You good?” She doesn’t even seem to hear me until she opens her eyes, smiling up at me and nodding.
She rises from the chaise, goes to her clothes and begins to dress.
I retrieve my extra shirt from the floor, folding it up as she puts herself back together. I pull open the bottom drawer, taking out some fresh pants.
I’m just putting them on when I look up at her, and she’s watching me curiously. I look down and realize my tie is falling off my neck.
Lissa walks over to me and pulls at the length of my tie, silently offering to help me tie it again. But the contact shocks me. The feel of her hands gripping my shoulders during sex was one thing. It was necessary leverage.
But this feels unpleasantly domestic. The touch of someone else’s hand against my chest is foreign and awful somehow, sending me reeling back into the past against my will.
I flinch away from her, stepping back.
I know it was just instinctive for her. Like breathing or blinking. But I can’t have this.
“Sorry,” she says immediately, snatching her hands away. “I’m sorry, Oliver. I forgot.”
I stare at her, watching the mortification bloom over her face. But the moment is destroyed, all the good feelings bleeding away, and I can’t fight the disappointment that consumes me.
I asked her to follow one rule, and she can’t even do that.
“You can go,” I say, hearing the coldness in my voice, and she doesn’t speak again, simply walks silently out the door.
Every part of me wants to call her back, to apologize, to explain. But I don’t. I can’t.
I won’t.