The Playboy's Proposition (9 page)
He said, “You can come when I claim another hole.”
I said, “I don’t understand, Master.”
He released my hips. I couldn’t see exactly what he was
doing, but in my peripheral vision, I saw him reaching for something on the
back of the couch. What was he doing with hands? What was that snapping sound?
He leaned over my back, stuck his hand into my face. He
said, “Suck my thumb.”
I was immediately hit by the smell of latex. I saw then what
he had been doing; he had put a rubber glove on his hand. I wondered stupidly
where it had come from, and what it was for.
I opened my mouth and did as he told me, not knowing what
the hell was going on, but determined to be obedient all the same. The gloved
thumb felt strange in my mouth.
“Get it good and slick,” he said. “Lots of tongue. There you
go. Good and wet like that.”
He pulled his thumb out of my mouth and stood up straight
again. With his other hand, he pulled back on one of my buttocks, then he laid
his wet thumb on my anus and rubbed around the puckered flesh.
He said, “This hole. I haven’t claimed it yet.”
I thought, fuck. I couldn’t speak. Every muscle in my body
tightened.
He chuckled and continued to circle my anus with his
saliva-slicked thumb. He pushed at my opening but didn’t enter me.
“You have such a pretty little asshole, and I want it. It’s
mine anyway. I won’t fuck this hole with my dick, not tonight anyway.”
He paused for a moment, then said, “But if you want to come
tonight, you’re going to have to beg me to stick my thumb in your ass.”
I moaned. No, please. This wasn’t something I wanted. Ever.
He started fucking my pussy again, sliding his big cock
slowly in and out in a slow and shallow motion. All the while his thumb circled
my anus. I squirmed under him. The pressure to come was fantastically intense.
I heard a spitting sound and felt moisture strike my anus. I
groaned. He had spit on me, to keep it wet and slick I deduced, but still ...
he had spit on me. I groaned again.
Michael pulled farther out of my pussy and increased the
speed and power of his thrusts.
He said, “You might as well let me take your little asshole.
It’s already mine, and I’m going to take it eventually, if not tonight, then
tomorrow, or the night after that.”
I continued moaning but didn’t say anything, torn between
wanting to push back and meet the cock sliding into my greedy pussy, and
pulling away from the thumb toying with my asshole.
He continued, “I wanted two things tonight. One was to see
you kneeling naked at my feet and taking my cock in your mouth. The other was
to fuck you as hard as I could and come with my thumb up your ass.”
I whimpered.
He chuckled. “Go on now. You know you want it. You want to
come and I want to shove my thumb in your tight little asshole. Make us both
happy and give me what I want.”
The pressure of his thumb against the opening of my anus
intensified. Was he going to do it anyway, no matter what I did? And it was
hard to think clearly with him pumping in and out of me, the tight pressure of
his dick inside me, sliding and sliding, the growing discomfort in my arms and
shoulders from the tightly-wrapped belt, and the heat inside me that demanded
release.
I had to come. I had to. How badly would it hurt when he
entered my ass? I didn’t know. No idea.
He did the grindy thing again. I moaned.
“Say it,” he commanded.
I didn’t have a choice anymore. I had to say it. Had to. For
him. For me. Surely it wouldn’t last for long.
I surrendered and said, “Okay, do it. Please let me come
first, Master. Before you do it, please let me come.”
“That’s not the deal,” he said. “Beg me to claim your last
hole, and then I’ll let you come ... at some point, when I say.”
I groaned while he let out an evil-sounding chuckle.
I was forced to relent. “Please, Master, stick your thumb in
my ass.”
“Do you really want me to?”
I didn’t see how this taunting was necessary, but I said,
“Yes please, Master. I really want you to claim me, my last hole. Please.”
Surely that would be enough.
It was.
He said, “It would be my pleasure, my sweet.”
I steeled myself for the harsh invasion I expected to come,
but instead Michael stopped fucking me, leaving his cock nestled tightly inside
my pussy. He spit on my asshole again. Instead of shoving right in, he slowly
pushed his thumb gently into me the tiniest bit, just barely opening my anus,
then he pulled out again. He went very slowly and carefully, pushing into me a
short ways, then pulling out. In and out. Again and again.
It would have been better, I soon realized, if he wouldn’t
pull his thumb all the way out each time. It was the incessant opening and
closing of my anus that was disconcerting. In fact, it was maddening.
His breath had grown louder and faster behind me, so I knew
he was enjoying drawing this thing out. I could imagine his eyes locked on my
clenched anus. I felt his pleasure at forcing me to grant him entry. He would
take his time, I feared.
He said, “Much as I enjoy you clamped so tight around my
dick, Sweet, you’re going to want to relax your muscles, especially the ones in
your ass. You’ll enjoy this more if you do.”
He continued to work his thumb slowly in and out, going a
little bit farther in as he progressed in opening me up. I focused on relaxing
my muscles again, and tried not to focus on what he was doing back there. It
was not a comfortable feeling. It didn’t hurt, but it wasn’t comfortable
either. Open and close. Open and close. Truly, truly maddening.
He praised me when I had relaxed my muscles to his liking. I
realized I had begun making a funny kind of high-pitched sound. I didn’t know
when it started. Every time he pushed into my ass further, I would make that
little sound. I couldn’t seem to stop it, even after I realized I was doing it.
Michael certainly paid it no heed. He was too focused on his
task. Every so often he would spit to add more moisture, then he’d continue
tormenting me. I listened to his harsh breathing and tried to think about how
turned on he was. I made my little noises and Michael happily toyed with my
poor asshole.
It took forever, but eventually he pushed his thumb all the
way inside of me. He didn’t move his hand for a few moments.
He said, “It looks even better than I thought it would.”
I made the funny little noise and managed to bear what he
was doing, because it was what he wanted of me, because it excited him. Without
thinking those thoughts, I would have begged off long before, coming or no
coming.
I nearly cried with relief when I realized he had hit the
limits of his restraint. He yanked his thumb all the way out of me then shoved
it hard back into my ass. I squealed, but was thankful for the discomfort that
meant it would soon be over.
He did it again, cramming his thumb into my asshole. Then he
began pumping his hips again, driving his cock in and out of my pussy. I
welcomed the distraction of his dick moving inside me.
He wiggled his thumb around in me while he thrust his hips a
few times, hard as hell, against me. Then he’d stop and do that grindy thing.
Then he’d pull out his thumb all the way, then ram it back inside me. Out, then
ram in again. Then a third time out and in. This began a pattern of thumb
wiggling, hip thrusting, hip grinding, thumb pulling and ramming, pulling and
ramming. Over and over.
I keened. The pain, the discomfort of the restraints,
combined with the need to orgasm was too intense. He had to release me soon.
I panted and keened. I heard Michael’s grunts and his
labored breathing as he worked over me.
Would he end this if I begged for mercy?
Finally, when I was beginning to wonder if I would survive
another thrust ...
He drove his thumb into my sore asshole and commanded
fiercely, “Come!”
And God help me, I did.
Michael’s orgasm followed quickly behind mine. As soon as
the shudders left his body, even before our heart rates slowed and our
breathing calmed, he snapped off the rubber glove, released my bindings, sat
down on the sofa and scooped me up into his arms.
I cuddled in close to him, laying my head on his shoulder,
inhaling his musky scent, comforted by the way he wrapped his arms around me
and petted me and soothed me with words of praise, telling me I was beautiful
and sexy.
The aftershock tremors of my orgasm pulsed through my body.
I was satiated and limp, had been filled with him.
It was a moment to want to be in love. And I let myself feel
it, to think I was in love with him, to float in the possibilities the belief
offered. He held me close, and cherished me.
Later, he carried me off to my bedroom. We kissed and he
stroked me all over, and he allowed me do the same to him. The sex was vanilla
and sweet and slow, made poignant by the preceding roughness in the living
room.
We dozed afterwards, wrapped together, until nearly four in
the morning, when Michael finally roused himself and went home. I snuggled up
to his pillow and slept with what remained of his scent next to me, and left my
mind open for him to find me in my dreams.
The next morning, I awoke a different woman than I had been
the day before. I was reborn with a new clarity, an understanding of myself and
my desires. Also, I thought I might be in love with Michael Weston, and love
can make you feel worthy and wise, regardless of what might actually be the
truth.
It was Saturday, so I didn’t have to work. I ate breakfast
and fiddled around with a few chores. It wasn’t even 10 o’clock when Elaine
called me, checking in to see how I had survived the fallout from the previous
evening’s events.
I told her that Michael and I worked everything out, but
didn’t mention anything regarding what Michael had confided to me concerning
his past and Gibson.
Elaine was put out that Gibson didn’t appreciate her
rational that I shouldn’t have to choose between him and Michael as long as I
wasn’t with both of them at the same time.
When I told her I wouldn’t be seeing Gibson again, she gave
the standard good-friend response, exclaiming that it was his loss.
As for what had happened between me and Michael, she sounded
surprised that I was getting away from the whole debacle without any
punishment. I explained that I wasn’t getting away with anything, that I was
being forced to wait for my punishment. I had no idea when it would be coming
or what it might be. She empathized with me and said Michael was an evil
bastard. I laughed.
She thanked me and my “perky boobs” for inspiring Ron at the
restaurant, and gave me a brief rundown of precisely how richly Ron had been
inspired once they got home. She sounded pleased that her nipples would be sore
for days.
When I hung up, I regretted being reminded that I had
punishments coming. Here I had been all happy and chirpy like Snow White with
her woodland friends, flouncing through some light housework at the dwarves’
cottage ... and then blam! You’ve got punishments coming. What a buzz-kill.
I wasn’t allowed to forget it again, either. Michael
e-mailed me around noon. I hadn’t necessarily been expecting more honeyed words
and tender love talk from him, but I wasn’t expecting what I got, either.
He wrote: “My Sweet, I won’t be able to see you again until
Monday evening. Please write and let me know if you’ll be available. It’s a
pity your punishment will have to wait until then. Those two days will,
however, give me extra time to consider all the ways in which you’ll pay for
your serious infractions last night. You will wish I had been given less
time. --- M”
Gulp. I suddenly recognized how sore I was, my nipples and
pussy and, embarrassingly, my ass. Funny how they hadn’t hurt before I got
Michael’s e-mail.
I wrote him back that I would be free Monday evening. An
hour or so later he responded that I would be given instructions about when to
be ready, etc., sometime on that day.
He added: “Continue to masturbate as before, at least three
times a day, then once Monday morning. Don’t forget to fantasize about someone
watching you. Also, I want you to add some anal play into your fantasies. I’ll
enjoy thinking of you, over the next few days, imagining me toying with your
tight little asshole. -- M”
Well hell. He didn’t ask for much, did he?
Over the course of the next few days, I did exactly as he
asked. There were a few hitches, though.
The first was that, thanks to my earlier habits, Gibson
still wanted to pop up as the voyeur in my fantasy scenes with Michael. I’d be
thinking hard about some dark stranger lurking in the shadows of my bedroom,
determined to keep him a stranger, but then he’d step toward the bed where
Michael had me pinned down, and I’d see that the stranger was Gibson. Damn.
I hated it. I seriously did not want that man in my
fantasies anymore. It’s not like I’d found out he was a serial killer or
something; I’d just learned that he was selfish, dishonest and unfeeling.
Pretty bad stuff, but not criminal exactly.
All the same, I had no desire to see him in my imagination
again, and his appearance there was disrespectful to Michael in more ways than
one.
I focused hard on banishing Gibson from my thoughts. It
wasn’t difficult remembering that Gibson was a bad man, recalling Michael’s
heart-wrenching account of the wrongs Gibson had heaped on Michael and his
family. I hoped I never saw Gibson again, and could only wonder how I had ever
been so easily seduced by him.
Once I removed Gibson from my fantasies, and had permanently
replaced him with a dark stranger who never left the shadows, I had to face the
second hurdle: anal play.
I hated the words, “anal play.” They implied there was fun
to be had. What Michael had done to me with his thumb had not been the least
bit fun. At best it had been uncomfortable, and at the worst, once he started
really pumping into me, fairly painful.
Yet, I wouldn’t go back in time and change it, stop him from
doing what he did. Because he did that to me, because he demanded it of me, and
because I gave it to him and took the pain for him, I was swept to a new place,
a new understanding of what it was to be a sub.
I felt that I was released from many of the insecurities and
fears that had been holding me back. I connected to Michael in a deeper way,
and I believed the same happened for him.
So even though I greatly anticipated the ways my D/s
relationship with Michael might continue to grow, I thought it might be
impossible for me to ever enjoy anal penetration. I would try, though, for him.
I did as Michael asked, and added ass play to my
masturbation fantasies -- kind of, sort of. Because the thought of him sticking
anything in my butt immediately destroyed my arousal, I eventually had to
settle on him just touching the outside of my anus. A few times, I even let him
stroke me there. I did my best, and hoped it would be enough.
By Monday morning, I had completed all my homework and
judged myself to have a perfectly clean conscience. I was excited to see
Michael again and tell him what a good girl I had been, and did my best not to
roll my eyes at myself whenever I thought the “good girl” part.
I hadn’t forgotten that I had those damn punishments coming,
and when Michael’s e-mail arrived Monday afternoon, his instructions seemed
ominously formal to me, which made me worry all the more.
I stopped by my apartment after work, showered and dressed
in a casual skirt and blouse, without underclothes of course, then headed back
out. The directions Michael had given me to his apartment were easy to follow
and I had no problem finding the building.
It was a new building, all shiny with glass and chrome. I
thought it suited Michael well. I gave my name at the security desk, and the
guard rung up to Michael’s place, clearing me for entry.
I took the elevator to the top floor. There weren’t many
apartments on the floor that I could see, and quickly found Michael’s place.
The door was unlocked, as Michael had said it would be. I
stepped into the foyer and locked the door behind me.
The lighting was dim, the luminosity of the recessed lights
having been turned low. It smelled of furniture polish and floor wax, mostly
smothered under the heavy spice of incense.
It was a large entryway, the walls painted in a pale gray,
the trim white, the floor a gleaming black marble. On down the entryway, a
couple of closed doors lined the hall, then the space opened up into a large
living room, I presumed, judging from the white sofas and chairs.
I was extremely curious about Michael’s apartment, and
wanted to see more of it, but I didn’t waste any time inspecting my
surroundings for fear of risking his disapproval. I went straight to doing as I
had been ordered and placed my purse on the table that stood against the wall.
I pulled off my shoes and put them under the table, then I
removed my watch and earrings. I stripped off my clothes, folding them up
neatly and putting them on the table next to my purse and other belongings.
I shivered. The room was a little cold, I thought. Or maybe
I was afraid of what was to come. Or what if I was in the wrong apartment? Oh
hell. Why had I thought that? No, this had to be the right place. Everything
was as he had said it would be. I needed to calm down.
A small, white porcelain bowl sat on the table, and inside
it was a narrow tube of lipstick, precisely as Michael had said there would be.
I picked up the lipstick, and using the mirror that hung over the table,
applied it to my lips. It was very red, I thought, more red than I ever wore.
Plus, it was a lip stain type product, not actually lipstick, the kind of stain
that doesn’t rub off easily.
Next, although I thought it was strange, I followed orders
and rubbed the stain on my nipples and areolae, trying to keep the edges as
smooth as I could in spite of the poor lighting.
When I was done, I studied the effect in the mirror. I hated
it. It looked whorish, the dark red lipstick making my nipples and areolae
stand out so glaringly against the whiteness of the surrounding skin. And they
matched my lips. Ugh.
I couldn’t imagine why he wanted me this way. But it didn’t
matter what I liked or didn’t like, I reminded myself.
I picked up the four black leather cuffs that Michael had
left for me on the shelf below the table top. They were thinly padded on the
inside, with chrome rings attached all around the outside. The ankle cuffs went
on easily, but the wrist cuffs were more difficult since I had to close the
chrome buckles one-handed.
I stepped away from the mirror and onto the cold, hard
marble. I got down on my knees and assumed a kneeling pose, my butt resting on
my feet. I kept my knees spread open, my back straight, head up, eyes down,
arms at my sides, hands flat on the tops of my thighs. Exactly as he had
instructed.
Then I waited.
And waited.
I was cold, and the hard marble played havoc on my knees,
shins and feet. The thick leather cuffs dug into my ankles and butt cheeks. I
knew, realistically, that not much time had passed, but my growing discomfort
disagreed with that assessment. My body believed I had been in this pose for
ages.
I tried to concentrate on some breathing exercises that
Elaine had told me about. I focused on taking slow and steady breaths through
my nose, holding for a short count, then breathing out through my mouth. It
helped to calm me, and distracted me from my aching knees.
I thought I wanted Michael to hurry up and get me off this
floor ... until I actually heard his footsteps approaching. My stomach clenched
in knots, even flipped a few times. Punishment. My punishment would arrive with
my lover. Hell.
I warned myself to stop being such a drama queen. It was
ridiculous. How bad could it be, really? I mean, I had limits on this stuff.
Granted, Michael hadn’t asked me what those limits were, but I’d let him know
if he went too far, and he would honor that.
I kept my eyes on the floor. Michael stopped in front of me.
He wore a pair of heavy black boots and black leather pants, all I could see at
the moment.
Michael stood there for a few beats then said, “You may look
up and greet your master.”
I lifted my head and my stomach turned a few more flip
flops. Michael loomed over me. His leather pants were well-aged and snugged his
muscular legs and slim hips to perfection. He wore a loose-fitting white shirt,
untucked, the front unbuttoned to more than halfway down his torso, revealing a
swath of taut chest and abdominal muscles.
His black hair was pushed casually behind his ears as usual,
and the ends of his hair curled below the collar of his shirt. He looked
rakish, swashbuckling even. My playboy had turned into a marauding pirate.
He was crazy hot. Too hot for the likes of me. He should
have been holding a sword in his hand, ready to board and loot a Spanish
galleon, to plunder the dark-eyed Spanish señoritas trembling in the cabins.
He wasn’t holding a sword, of course, but that didn’t mean
his hand was empty. He was, indeed, holding something, though, something long
and thin, and he was tapping the end of it against the side of his calf. I
tensed. It was a riding crop.
So much for the sexy pirate, I thought.
Michael glowered and said, “The greeting? Will it be coming
some time today or do you need prodding? You don’t want me to prod you, Sweet.”
I snapped to. “No. Right. I’m sorry.”
I tried to remember what he had written in the e-mail, what
I was supposed to say. “Good evening, Master. I humbly present myself to you
for your pleasure and for my punishment. I deeply regret being ungrateful and
disrespectful to you. I freely accept whatever you do to me in the hopes that
you will forgive me, and give me the chance to serve you better.”
