Whips Or Kisses

Did you ever just have one of those real shitty weeks? To think how
good it started. In the hotel room with my hot new piece of ass
assistant. Wow, what a body on Holly. Took awhile to convince her
that the way to employment security involved being able to move
horizontally and not vertically. Well, not really, she was pretty
good cow girl style right up until my wife burst into our little
love nest. To think Holly even left before I had a chance to finish, that
bitch. I almost couldn’t wait to fire her.

I knew the wife was pissed but even I was surprised when she said
she was leaving. Now being an executive, it wouldn’t due to have all
of this come out. I had been cheating on her for years. Hey, women
are like new cars right? Every now and then you wanted that new car
smell and just the feel of a different sportier ride.

Still, I had to get this smoothed over. Determined to get her to
drop this divorce nonsense, we sat down to talk about it. Now she has
always been a quiet one, I liked it outside the bedroom because I
always got my way, but hey, it gets old in the sack you know.
Tonight she seemed a little too calm, and although I usually let her speak
first, she waited so long that I felt I had to break the
silence. “Listen, I know I made a mistake and it won’t happen
again.” I figured that was safe, she didn’t need to know that my only
mistake was in getting caught. Now I thought, hear come the tears, but
instead she said simply, ” I want you to see a Doctor.” “A doctor?,
there’s nothing wrong with me.”

“This is not open for discussion. I have already made your first
appointment. You need to be there tomorrow at 1 PM. The appointments
are $500 an hour and are not covered by our insurance, you can pay
them out of the money you were spending on hotel rooms. If you don’t
go, I have an appointment at 4 with a divorce lawyer.”

I thought about it and what the heck, $500 wasn’t going to be too
much of a problem. I figured anymore I wouldn’t get a hotel room and
just go back with the woman to her place. This would end it pretty
quick and was a lot more reasonable than I expected her to be, so I
agreed. “Ok, who is the doctor and where is he located?”

“Her name is Olivia, and here are the directions.”

At 1 o’clock the next day, I made my way over to the Doctor’s office
and when I entered the first thing I noticed was this extremely
feminine acting male receptionist. Great, a fudgepacker I thought
but
told him I was there for my appointment. He walked me back to a
closed door, and told me to go in as she was expecting me. As I
entered, I was stunned at how young this doctor was, and how
attractive, now all of a sudden, the $500 was seeming like a good
investment. She was on the phone and as I noticed no wedding ring, I
barely heard her say something about “yes, he’s here.”

We had a pleasant conversation while she asked me questions and
filled out forms. She had such a wonderful voice, the more I talked
to her the easier the conversation became. She asked about all the
times I cheated on my wife, and she was really cool about the
answers. Didn’t seem to bother her at all. It felt so easy to just
open up to her. She asked if I had come here with the idea of
changing and I told her not really. I was just trying to keep my
wife happy until this blew over. Again, she took it in stride, she even
seemed to be flirting with me. She had already told me she thought
she needed to find out first hand why all these women seemed to want
me. Finally she told me it was time to move on to the physical. As
she came around the desk, I could finally see her long legs coming
out of the oh so mini-skirt she was wearing. I thought she was going
to hand me a specimen cup and instead I got a cup with a little blue
pill. Suddenly her hand brushed up through my groin and her hand
groped around my already hard package. She just looked me in the
eyes with an evil little smile and said “looks like we don’t need it, but
we do have a few hours to kill right?” Now go on in and get
undressed and I will be in shortly.

I walked into the exam room and immediately started to strip. This
is great I thought, not only is my wife going to be happy, but I am
going to be banging this sexy doctor while she thinks I am being
cured. I took the viagra and she must have made me waiting for 30
minutes because when she walked in, I was flying at full mast. She
came in closer to me pushing me back on the exam table and putting a
cold stethoscope over my nipple as she leaned in to listen to my
heart. “It’s racing she said” as I breathed in her perfume. “Must be
the company I said.” All the while my dick was rubbing up against
her outfit, driving me crazy. “I bet you’re thinking the same thing I’m
thinking aren’t you she purred, do you me to?” Oh yes, I replied. “I
like to be in control”, and she pushed me back on the table,
straddling me, pushing my arms up over my head and then a sudden
feel of cold as two restraints clamped down on my wrists. And then she
reversed herself, and I found myself so close to the source of her
musk that I was now able to catch a scent of. Yet I couldn’t move
closer to her with my arms restrained. Her hands moved down my legs
again guiding them into restraints, and now I could no longer move.
Of course, where did I want to go, right now, all I wanted was to be
there with her and wait for her to complete her seduction.

She slithered off of me and turned and with that same evil grin,
just looked at me and asked if I was “comfy.” “Good.” And with that she
slipped a condom on me and two latex gloves on her hands and she sat
on a stool. She put lubricant on each of her gloves and with one
hand she continued to manipulate my member and with other she reached
underneath and began to probe and gradually enter my anus. The
feeling was incredible and she asked me if I enjoyed her way. I was
in heaven and told her so. I could feel a second and then a third
finger enter me, all the while her other hand continued to bring me
closer to orgasm. “Do you want to have the most intense orgasm you
ever had?” She asked. I couldn’t believe anything could make me feel
better than I did right now, but if she was this right so
far…. “Yes!
Do whatever you want to me.!” “I was hoping you’d say that.” She
removed her fingers from inside me and I quickly felt another object
being inserted, it opened me wider at first, but then I felt my
muscles contract around it. “Don’t worry, she cooed, it’s just your
sphincter closing around it to hold it in place.” With that I heard
the gentle buzzing sound and felt incredible waves of pleasure rush
through me. Olivia stood then and walked around to the side of the
table, I was writhing in ecstasy with her hand manipulations and all
of the other stimulation.

She leaned in closer to me, her lips brushing up against my ear as I
felt her warm breath and heard her whispering, “you know, this dick
of yours gets you into all kinds of trouble doesn’t it, it feels
good, and this is all you want right, to feel this good, or even
just a little better right?” She increased her stroking and I knew I was
going to cum. “yes I told her, yes.” “That’s your problem then, it
makes you selfish, all you want is your pleasure, so go ahead, feel
that pleasure, c’mon, cum for me, c’mon.” I lost it, my semen
erupted into the condom and I felt contraction after contraction as she
pumped me, and as she did, I could feel my ass muscles tighten
around what ever she had put inside me, and I felt a warm sensation inside
me, that quickly escalated into a burning sensation, and the pain
increased and I snapped out of moment of heaven, screaming that she
was hurting me, struggling to get out but not being able to, and as
the tears started, she slapped me, told me to shut up and stuffed
some kind of gag in my mouth.

I gathered myself as together as I could, my eyes were still
watering from the pain. My insides were on fire. “I didn’t hurt you she said.
You did it to yourself. That butt plug inside you holds pepper
juice. As long as you don’t orgasm, it will make you feel good, but you are
the one who wants the orgasm. You are the one being selfish. As soon
as you start to orgasm, your muscles contract and force the juice
into you. You need to learn to control your need for pleasure. It
didn’t have to be a painful lesson, but you said you didn’t want to
change and some lessons are therefore painful. Now its time for your
next one. This is the semen you ejaculated. A rather impressive
amount I must say, but then again, I have that affect on men. I want
you to show me that you are going to take a step towards changing,
by consuming this.” I shook my head NO. No way would I ever do that.

“Well, then we do things the hard way. She punched an intercom
button and told someone to come in.” My eyes bulged with the thought that
it might be her receptionist and who knew what was going to happen. It
was like she read my mind. Oh no, this is my new assistant, not
Rodger, he may be involved in later training, but not right now.

I heard the door open and when I saw Holly, I knew that I was in
serious trouble. Olivia gave her some instructions and then told
me “when you are ready to do what I want, have Holly call me.” With
that she left the room, and I was left with my former
secretary. “She climbed on me, already beginning to work on me as she had done earlier and she too came in close to me, reveling in my fear, and
simply said “so when I make you orgasm it makes you hurt, remember
all those things you made me do, I’m going to hurt you…. Boy am I
going to hurt you.”

And she did, no matter how much pain I was in, my penis didn’t seem
to care. She no sooner started paying attention to it, when I would
once again find myself crossing the brink into orgasm and into the
inevitable increase in pain. All the while, she collected my
ejaculate. Oh, she might smear some under my nose and tease me by
telling me to get used to the smell. And each time, through the
tears, she would ask me, will you do as Olivia wants.

Finally, I caved in. I nodded yes, when she asked me and as Olivia
removed my gag, she told me “beg me to drink your cum, beg and maybe
I can make the pain go away.” I couldn’t believe I was saying this
in front of Holly, but I begged her anyway, begged her to stop the
pain. That I would do anything if she would stop the pain.” Olivia told me
she had a salve that would cool the pain, but it needed to be
administered internally and that since I had been so stubborn, the
pepper juice had made its way deep inside me. She took out the salve
and began to coat a dildo with it and once it was coated, she gave
it to Holly who put it in her strap on harness. “If you thought it
burned before, just wait til the plug is removed. Once air enters,
the pain will get worse. Holly can make it go away, but you are
going to have to beg her to fuck you. You can ask her to fuck you deeper
and you better if you want that salve to reach all the burning
parts, but she will do as she wants. One thing she wants is to hear you
beg.” With that she removed the butt plug, not only did the air
start to make the burn worse, Olivia gave it one last squeeze on the way
out to empty its contents. I was on fire, and it wasn’t long before
I was begging Holly to fuck me, I was crying from the pain, pleading
and begging with her to make it go away and finally I felt the head
of the dildo enter my ass. There was some pain from the stretching
but the relief to the burning was almost pleasurable in going away.
But again, Olivia was right, deeper inside of me, I was still on
fire and I had no choice, I asked Holly to fuck me deeper and harder. She
varied her motions, sometimes helping ease my pain, other times
teasing me while waiting for me to beg for more. All the time
calling me her slut for wanting it so hard. Gradually the pain was going
away, and inspite of everything that had happened that day, I was
getting hard again, which prompted Holly to comment on how I
apparently liked it.

I heard Olivia chuckle off to the side and when I turned my head,
she had just finished coating her strap on with all of my semen from the
day. “Of course he does Holly, he is starting to learn that he can
take pleasure in pleasing women. Now it is time for him to live up
to his promise to me. If you don’t do this, I’ll have Rodger come in
and you can get your first taste from him.” With that, I gave up, I
could see the white coating the black dildo as she brought it into my
mouth, tasted the salty taste of something I swore as a man I would
never taste. All the while feeling Holly penetrate me in a way I had
never thought I would allow. And I licked and I tongued and I even
felt a little bit of pride when Olivia told me I cleaned up every
drop like a good little boy. I even felt the shudder from Holly as
she too reached her moment of climax and I felt good knowing that I
had made her happy.

As Olivia walked me out of the office, she told me that my wife
would report to her on my behavior between visits. That I had made a nice
start but we had a long way to go. I promised to be good and Olivia
just said “When I’m through with you, I will actually believe you.”