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Authors: Olivia Jake

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Master leaned
in to my ear and whispered, “Thank him for taking your coat, Jennifer. You
don’t want to be rude now, do you?”

I tried to
smile, as I looked Antonio in the eye, and said, “Grazie, for taking my coat,
Antonio.”

He lifted my
hand and kissed it again, then his eyes lingered on my breasts, and then down.
It was dark enough that I don’t think he could see my pussy, but it didn’t much
matter at this point, “It is my pleasure, signoria.” Master released his hand from
behind me and then motioned me to sit. As I started to turn around, I felt a
light slap on my ass. I didn’t even bother turning to see whose hand it was.

CHAPTER 23
 

When I slid
into the booth I was a ball of emotion. I was furious at myself, I was furious
at him. I wasn’t enjoying this. Yet as I sat there, across from Master’s
admiring gaze, something warmed in me. “You look beautiful, Jennifer.” He said
softly, and then added, “Put your shoulders back a bit more and put your hair
behind your shoulders so I can see you better.”

As if on auto
pilot, I complied. Immediately. I didn’t even hesitate or question what he was
asking me to do. There was a diffused spotlight from above and I could tell
that the way it lit the table, even though it was soft light, it still lit me
so that anyone who came up to the table would very clearly see my breasts. He
reached across the table for my far hand, the one closest to the wall. I think
he did this so as not to block the view of me from whomever might come over.

 
“Lift your skirt so that you’re not
sitting on it. I still don’t want you staining it.”

I complied,
but I was still angry, “Are you going to make me lick the booth after, too?”

His mouth
turned up, amused, “I’m not concerned about staining their leather, but if
you’re offering…”

 
“No, I’m not offering. I’ve licked enough
leather for one night, thank you.” and without much of a pause, I added, “Master.”
He smiled again and squeezed my hand.

 
“That’s a shame, because you looked so
nice doing it.”

 
“What part did you like best? Humiliating
me in public? Breaking my will to see if I would do something so debasing?
Showing me off to the valet first, and now to Antonio?” I couldn’t hide my
anger. I didn’t understand why someone who could be so caring could be so
hurtful.

 
“Why, all of it, of course.” He said
calmly. Then added, “though I don’t appreciate your tone.”

I tried to
check my tone. I knew it would only lead to more punishment. “Please don’t talk
to me like I’m a petulant child, Master.”

 
“I will treat you the way I please,
Jenny.” He knew I hated that name, but if after everything else he had already
put me through tonight, if he thought that would bother me, I was long past
that. “But if you act like a petulant child, I will talk to you like one. And
before you ask me how you’ve been childish, I will tell you so that we can put
this to rest and enjoy our evening. I have explained to you that, when we’re
together, I expect you to follow my orders. You came along willingly tonight,
so that means, to me, tacit understanding that you will do what I tell you.
When you refuse, to me, it’s no different than a child not doing what he’s been
told he must do.”

 
“But humiliating me?”

 
“You only feel humiliated because you
question my orders. I’ve told you before, it would be so much easier for you if
you didn’t question everything. There would be no emotion, or no negative
emotion. If I am your Master and you are my slave, then you would simply
comply, without thinking about how it makes you feel or wondering how it might
look to others. You would happily lick the seat because I told you, and then I
would praise you for licking it so nicely, which would make you feel good, and
that would be that.” He paused, took a sip of water and then continued,

 
“You see it as humiliating. I, on the
other hand find it incredibly sexy, watching you bent over, licking your own
juices off the seat, knowing that the valet and anyone else who saw you was
thinking what a gorgeous little slut you are and envying me that I get to do
whatever I want with you.”

I knew I must
be being brainwashed. I knew I was smarter than this. But somehow, he made
sense.

 
“Little bird, please, just try. I will
keep pushing you, you know that, don’t you?”

 
“Yes, Master. I do.” And I did. I knew
he’d keep pushing and I’d keep… what? Would I push back? Would I follow? I was
struggling with it all. Maybe I would be happier if I just gave in, surrendered
completely. I knew I was already surrendering my body to him. I had let him do
things to me that I’d never let anyone ever before do. But surrendering my mind
to him. I knew that was far more dangerous. I had no idea yet, just how
dangerous.

 
“I’ll try. I want to please you, Master,
I do. It’s just…” I couldn’t finish.

 
“I know you do, Jennifer. And you do
please me. Immensely.”
 
He must know
that’s all he needed to say for me to respond. “Finish what you were going to
say.” He said softly, but sternly.

 
“It’s just that, I’ve already given you
so much of me, Master, and you still want more. What if, when I’ve given you
everything, and I have nothing left to give, what then?” I couldn’t say the
last part, but the last part of that thought was: I’ll be left with nothing.
And then what?

 
“Jennifer, there are no guarantees in
life, are there? Are there any relationships that are 100% sure to last?” he
asked, and I shook my head no.

 
“Little bird, try this. For the rest of
the evening, don’t question what I tell you to do. See how it feels. If it
feels worse than when you do question it, then perhaps this is not meant to be.
But, if it feels better because you know that by doing what I tell you, you’re
pleasing me, then that’s your answer.”

He was so
convincing, so sure. I nodded and said simply, “Yes, Master.”

 
“Good girl.” He squeezed my hand and
smiled. Just then, Antonio walked up to the table.

 
“Stephen, would you like to see the wine
list? Or, oh, I know what you’d like. I have a special Barolo down in the
cellar. Mmm, truly magnifico!” he gestured with his hands.

 
“You know I trust your tastes, Antonio.
The Barolo it is then.” He smiled at Antonio and then at me. I smiled back,
relaxing. I should have known better. “Antonio, you say it’s down in the
cellar?”

 
“Si, si.” Antonio nodded with a slight
smile.

 
“I think Jennifer here would enjoy seeing
the cellar. Could I trouble you to take her down with you, just a quick tour?”
anyone else would think this an innocent request, but I knew what he was doing.
He was testing me, seeing if I could just follow his orders and walk through
the restaurant, practically naked, with a stranger. At least, that’s all I
thought it was at first.

 
“Of course, it would be my pleasure.”
Antonio said as he held his hand out. Without hesitation, I took it and smiled
at him. He tucked it into his arm and patted it, then turned to Master and
said, “I won’t keep her too long, Stephen. We’ll just let her get a taste.” He
paused, “Of the cellar.”

 
“Take your time, my friend. Enjoy her
company. You’ll see, she is truly lovely.” My back was turned as I heard him
say this. I was grateful he couldn’t see my expression or my face flush. I
stood as tall as I could, shoulders back and I tried not to question whether my
Master had just pimped me out to his friend.

 

Antonio and I
walked in silence through the restaurant. While I didn’t know this man, I was
comforted to have him to hold onto. I tried to focus on the restaurant, the
details, the furnishings, rather than the few tables of people who may or may
not be looking at me and seeing everything. It was fairly dimly lit, and we
were already in the back, so there weren’t too many tables between our booth
and the cellar. Still, I knew I was gripping him tightly, but I didn’t care. I
truly understood the phrase, ‘Any port in a storm’.

 
“You are nervous, bella? Or do you always
hold on so tight?” his voice was smooth and low, and his accent was somehow
comforting.

I chuckled a
little, “I’m a little nervous, I guess. Embarrassed too.”

 
“Why, bella? Are you afraid of me? Do I make
you nervous? And what do you have to be embarrassed about?” as he asked this,
he turned to face me, and he stroked my cheek tenderly. I actually closed my
eyes.

 
“Yes, I’m sorry. I don’t mean to offend
you.” I couldn’t believe I was apologizing to him for being nervous. But he
hadn’t done anything wrong. Yet. “And, um, my outfit… I’m not sure what people
can see.”

He smiled,
“They can see a beautiful woman. There’s no reason you should be embarrassed
about that.” It sounded so rational… “And you’re afraid too? What are you
afraid of?”

 
“I don’t know why Mast-, um, Stephen sent
me down to the cellar with you. I don’t know what he wants me to do.”

Antonio
chuckled and started leading me forward again, “But you came with me, no?”

I nodded, and
before he could ask, I said, “Because he told me to.” As I said this we reached
a door. He fished out a key and opened it, turning on a bright light that
illuminated a brick cellar.

He turned to
me and said, “Then you know what he wants you to do, bella. You heard him. He
and I have the same tastes. In wine. In women.” I knew that I turned bright red
and my fears were justified.
 
“You
don’t want to disappoint him, do you?” I shook my head no. “Good girl.” He said
and led me down the cement stairs into the cellar. I heard the door close, and I
knew at this moment that Stephen brought me here to get fucked by Antonio. And
I knew that because he wanted it, I would do it.

When we got to
the end of the stairs, the room itself wasn’t more than maybe 15’ x 15’, and
most of the space was taken up by wooden racks of wine. Antonio was still
behind me, and now his hand was cupping my ass, stroking it. He pressed himself
into my back and I could feel his hard on as he reached around and with one
hand started pinching my nipple, and the other reached up under my slip to
start stroking my pussy. “Mmm, bella, Stephen was right, you are lovely, and so
nice and wet and ready for me. You’re no longer afraid of me, are you?”

I shook my
head and said, “No, Antonio.” To which he quickly pulled back and slapped my
ass, hard.

 
“Show me some respect and call me Sir. Or
Master Antonio.” He said forcefully. I don’t know why this didn’t upset me.
Perhaps I was so used to it by now with Master.

 
“I’m sorry, Sir.” I said meekly.

 
“Now, turn around and face me.” He said.
I did, and I looked down, unsure if looking him in the eyes would be another
sign of disrespect. “I wanted you to suck my cock, but I know how Stephen gets,”
he chuckled a bit, “and he’ll be very disappointed if you tear your stockings.
Isn’t that right, bella?”

 
“Yes, Sir.” I whispered, still not
looking at him. He started fondling my nipples again, pinching them through the
thin fabric.

 
“Then in that case, bend over so I can
fuck you. Put your hands on the stairs there.” I did as I was told as he moved
behind me, lifted my slip, unzipped his pants and rubbed his cock against my
pussy lips.

 
“This is going to be quick, cara. I have
to get back to work, so I’m going to fuck you hard. Hold on.” And he wasn’t
kidding. He thrust his cock into me in one quick motion. I gasped. He wasn’t as
long as Master, but he was wide. And rough. He fucked me hard, and I hate to
admit it, but I was enjoying it. I started moaning and moving back, meeting his
thrusts. I couldn’t believe how my body responded. Then he reached around and
found my clit, and I moaned loudly. I think he might have laughed, but it
spurred him on harder, if that was at all possible. He found just the right
spot on my clit and as he rubbed it, his cock started hitting my G-spot and all
the emotion of the night so far, everything that was bottled up inside me
started welling up as I started tingling and I felt my orgasm start rolling
over me and as I came all over his cock I screamed which must have pushed him
over the edge as his hands gripped my hips even harder and he moaned as he
came.

When he pulled
out, I felt an emptiness. I was still in somewhat of a daze and stumbled a bit.
Thankfully, he was still holding me and he laughed, “Careful, cara.”

 
“Thank you, Sir.” I don’t know if I was
thanking him for catching me so I didn’t fall, or for fucking me so hard that I
came all over him.

 
“Stephen was right about you.” he smiled.
I wasn’t sure exactly what that meant and I didn’t want to ask. He let go of me
and reached over to grab a towel. He held it out to me and I sheepishly wiped
between my legs. I could already feel his cum dripping out. I tried not to
think about the fact that I let a total stranger come inside me. He broke my
thoughts as he said, “I’m going to grab the Barolo, bella. I’ll be right back.”

When he came
back he gestured for me to go up the stairs. This time, when we walked back
through the restaurant, I walked in front of him, my head held high, shoulders
back, as I knew my Master would want me to. When we got to the table, I looked into
Master’s eyes and saw how proud he was of me. I knew how happy I had made him
by doing what he told me to do without questioning. He smiled at me and the
warmth that rolled over me was unexplainable.

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