Jennifer's Surrender (10 page)

 
“The key to anal play, Jennifer, is for
you to relax. Your instinct is going to be to tense up, but if you relax and when
it feels like you should tense, push out, it will be very pleasurable.” He said
as he pushed his finger in and out, simultaneously stimulating my pussy.

 
“Mmmm, it feels good, Sir.” I was
completely relaxed and enjoying the new sensation.

 
“Good.” He said as he continued. I felt a
little more cool liquid and then more pressure, “Relax, angel, just relax.” It
was so nice hearing his terms of endearment, I couldn’t help but give in as he
pushed what I assumed was a second finger in.

 
“Uunhh” I moaned, “oh, that feels good.”
I couldn’t believe how good. He was pushing two fingers in and out of my ass as
another finger started stimulating my clit. “Oooooh, Sir, oh, that’s so good.”
I tried to move my hips but between the strap around my waist and thighs, I
couldn’t move at all.

 
“Do you like that, little bird? Do you
like my fingers up your ass while I play with your clit?”

 
“Oh, yes, Sir. Yes, I do.” I’m sure he already
knew the answer…

 
“I’m going to make you come, little bird.
Are you ready?” he asked rhetorically as he increased the pace of his fingers
in my ass and finger on my clit and then suddenly shoved his cock in my pussy.
The feeling was incredible. I was so full between his huge cock and the fingers
up my ass, it felt like sparks flew as I orgasmed. As I started to come down
from it, he slid his cock out of my pussy and another finger up my ass,
producing another low moan from me.

 
“Ooooh, so full, Sir.” I said but it felt
so good and he continued pushing his now three fingers in and out, in and out,
as my pussy still tingled from its orgasm.

 
“Yes, I know sweetheart. It’s so full
now, but just you wait, it’s going to be amazing when my cock is in there. Tell
me, angel, do you want my cock up your ass?” his other finger started circling
my clit again.

 
“Oooh, yes, Sir, yes, I want you to fuck
my tight little asshole.”

 
“Mmmm, such a naughty little girl you
are. I don’t know, I don’t know if you’re ready for it.”

 
“Oooh, please, Sir. Please, I want your
cock up my ass, please.” I heard him laugh.

 
“We’ll see. I think you need to come
again. Do you think you can do that for me?”

 
“Oooh, yes, Sir. Whatever you want, Sir.”
I was so lost in the moment, but it was true, the sensations I was feeling, he
could have done whatever he wanted.

 
“That’s right, dear. And what I want is
for you to come again. Then we’ll see if you can take my cock up your tight
little ass.” And with that, he shoved his cock in my pussy, now with three
fingers up my ass.

 
“Aaaaahhh, soooo full. So full.” I was
barely able to speak as he started fucking me harder. His cock was already so
damn big, but the combination of it and his fingers up my ass, I felt like I
was going to explode. His cock started rubbing against my g-spot and I could
feel my orgasm rising, tingling, and when I came, I felt it not only in my
pussy, but also in my ass.

 
“Mmmm, that was a very good one, little
bird. I could feel your ass spasming as you came. I can’t wait to feel it
around my cock.”

I was still
panting from coming as he slowly pulled his fingers out of my ass and I
whimpered. It suddenly felt so empty. Then, I felt cool liquid again, and while
I couldn’t see anything, I assumed he was lubing up his cock. Sure enough, I
soon felt its big head at my tiny opening. “Relax, angel, relax.” And I tried
to, but he was so big.

 
“You’re too big, Sir.” I pleaded. It felt
like he was going to rip me in half as he continued to push his head in.

 
“Flattery will get you nowhere.” I could
hear the smile in his voice and I relaxed and laughed, and as I did, he slid
his head in.

 
“Aaaaahhhh” it burned, but he didn’t
move. He waited until I relaxed again, when the stinging stopped, and then he
slowly, inch by inch started to push more in.

 
“Push out, Jennifer. Push against me.” It
seemed like it would do the opposite of what he wanted, but the more I pushed
out, the more I opened up and he slid in.

 
“Uuunnnhhh.” I moaned, but now, now it
was a good moan. His fingers up there were one thing, but this, oh, this felt
incredible. “Oooh, Sir, it feels soooo good. Sooo good.” I said as he slowly
slid in and out, in and out, getting farther and farther in each time. I felt
like I could feel his cock up into my throat, that’s how full I felt. But the
sensation was unlike anything. Finally he was all the way in. And then he slowly
started fucking my ass. As he slid his cock in and out, I couldn’t believe how
good it felt. I wanted so badly to be able to move back and forth to meet his
thrusts. But no matter, the more he fucked me, I started feeling another orgasm
rising.

 
“Oooh, Sir, oh my God, oh my God, Sir, oh
my God, I’m going to come, Sir, you’re going to make me come, Siiiiirrrrr” and
as I came I wailed, moaning so loudly I could barely hear him grunting as he
came.

I couldn’t
stop saying “Oh my God” over and over, like it was a meditation chant until
after a few minutes he pulled out and I felt so empty. He started unfastening
my legs and arms, and then stood in front of me to help me off the bench. Thank
goodness he did because my legs collapsed at first.

Once again, he
led me over to the bed and we lay there as I regained whatever semblance of
composure I could. I could feel his come dripping out of my ass as I turned
over to face him, “That was amazing. Thank you.” he smiled and chuckled.

 
“I’m glad. You seemed surprised that you
could come from anal sex.”

I laughed,
embarrassed, “I had no idea. But oh my God, it was so intense.”

He smiled, “I
take it you’ve forgiven me for this morning, and understand I’m a man of my
word?”

 
“Yes, Sir.” I said sheepishly, like I was
a fool for ever doubting him.

As the sun
started to set on Sunday, I got dressed in the clothes that I had arrived in a
little more than 24 hours earlier, yet given everything that we had done in
that span, and the range of emotions I had been through, I couldn’t believe
only one full day had elapsed. It was odd feeling fabric against my skin,
probably because everything was sensitive and sore. I was aware of every
movement, whether because of the rough denim rubbing against my marked ass or
bra straps pressing against sore shoulders or the bra itself rubbing against my
nipples, I could feel everything. Funny, whereas I was first uncomfortable
walking around naked, now I was uncomfortable in clothes, though the former was
in my head, and the later was completely physical. Still, one more reminder of
a quick change in perspective and preference.

Sir walked me
to my car. I realized I was sad to be leaving his house. Before I opened the
door he turned me to him and drew me into a deep kiss, much like our first
kiss. It felt so good, so normal, and so loving. My hands weren’t bound, I
didn’t have any rules, any posture I had to keep, I just surrendered my lips to
his. As we broke apart, after a few more tastes of each other’s lips he stroked
my cheek.

 
“I had a wonderful weekend, little bird.”
he traced my face and pushed a bit of hair behind my ear.

 
“Thank you, Sir. I did too.” I grinned up
at him.

 
“Good. Then you want to continue?” I knew
enough not to laugh at the absurdity of this question. ‘Continue’ was such an
odd way to ask if I wanted to keep seeing him, but I guess a lot of what we had
done that weekend would be defined as odd…

I nodded,
still smiling “Yes, Sir. Very much so.”

 
“That’s wonderful to hear, Jennifer. Then
I’ll see you here Friday night after work and you’ll spend the weekend here
again.” I was about to say something but he wasn’t finished, “Now then, you are
not allowed to touch yourself or masturbate during the week. Do you
understand?” I furrowed my brows and opened my mouth, then quickly closed it
and swallowed before I replied meekly, “yes, Sir.”

 
“Good girl. I’ll know if you break the
rules, you know that, right, Jennifer?” I nodded. “And you know that I’ll
punish you, and I mean really punish you, if you do.”

 
“Sir?”

 
“You haven’t been truly disciplined yet,
Jennifer. What we did this weekend was play. Any pain was all for pleasure.
When I really punish you, you’ll understand the difference.” His tone was
sobering.

 
“When? You expect me to break the rules?”
I asked, hurt that he didn’t trust me.

He smiled, “At
some point, you will. I set the bar high, little bird. I can tell that you’ll
always strive to reach it, but nobody’s perfect.” I nodded, determined that I
would make him proud.

He opened my
car door and told me to drive safely, sleep well and have a good week, just
like a normal boyfriend would. But Sir was not a boyfriend. And I wasn’t his
girlfriend. I wasn’t exactly sure if I was his sub yet. As I drove home, I
replayed all the things that we did, and yet, after all that, I still felt it
was presumptuous on my part to assume I was his sub. Perhaps it was because he
hadn’t yet made it clear that I was in his mind. But in mine, it was clear. I
was his and I would do whatever he wanted.

I slept like a
rock Sunday night. So heavy that I didn’t wake up in time for my normal morning
run, though I’m not sure I would have been able to run even if I had the time.
My body was still stiff and sore from the weekend’s activities. As I lay there
in bed thinking about it, my hand drifted down and I absentmindedly started
playing with myself. With my right hand on my clit and my left on my nipple I
was reliving the various things until my mind clicked and I froze. I wasn’t
supposed to be doing this. Would he really know? I was an awful liar, and I
didn’t want to lie to him. I stopped what I was doing and got up to shower. As
I lathered myself I worried that this would count as rule breaking. But it
wasn’t intentional! I vowed to have more self-control for the rest of the week
and hoped that he wouldn’t consider this a transgression.

By Wednesday,
I was a mess. I couldn’t stop thinking about Sir. I couldn’t read any of the
erotica that had recently been my escape, because if I did, I’d get even more
horny than I already was. I wanted to see him, I wanted to feel his hands on my
body. God, I would have settled for just hearing his damn voice. After such an
intense weekend, this radio silence was killing me. And with no release, I was
going nuts.

Thursday
morning’s staff meeting was embarrassing.

 
“Well that’s a lame idea.” I said,
realizing that what I was thinking actually came out of my mouth as all eyes,
and gaping mouths turned towards me.

 
“Jennifer, my office, now.” Bill said and
I knew I had royally fucked up. In the eight years I had been there, never had
I been called into Bill’s office like this. And of all the people I wanted to
make proud, I couldn’t believe that I said what I did.

I followed
Bill to his office with my tail between my legs. When I was safely inside he
growled, “Close the door.” Which I obediently did. I could barely make eye
contact with him.

 
“While I always appreciate honesty,
Jennifer, I don’t appreciate disrespect.” I had never heard this tone from him,
probably because I had never before put myself in this position with him.

 
“I’m so sorry —“ I started to say
but he cut me off.

 
“Save it. I’m not sure what the hell is
up your ass, but this entire week you’ve been a little bitch.”

This wasn’t
just an angry boss, this was something else. I had no idea at the time what it
was, but I knew better than to challenge him. It was rare to see Bill lose
control. In all the time I had been there, there might have been a couple of
instances that pushed him over the edge.

 
“I am going to chalk this up to long
hours on the Tutto account.” He said and then added, “You can leave now.”

I was shocked.
I did as he said and walked out. I wasn’t sure there was anything else I could
do to fix things so I just went back to my office and focused as best as I
could for the rest of the day. I now not only was frustrated sexually, but I
was worried that I had upset my boss and unsure what to do about it.

I tried to
make sure that I laid low Friday, grateful when the end of the day finally
came. I didn’t speak a word to Bill since Thursday’s reprimand and I was still
mortified.

As I drove up
the coast to Sir’s house, so much was swimming through my head that by the time
I got to the gate, I was a bundle of nerves. This time, as opposed to the
previous weekend, the nerves weren’t just in anticipation. I was pissed. Upset
that he had set out some arbitrary rules that I let affect me to the point that
I jeopardized my work. I was so tightly wound, I couldn’t believe that lack of
masturbating for a week could do that to me.

When I got out
of the car, I was loaded for bear. He came up and kissed me, but I was stiff.

 
“Is something wrong, Jennifer?” he asked.

 
“Can we have a drink first?” he looked at
me and I rolled my eyes, in no mood for his bullshit, “Sir.”