Rachel's Dilemma Ch. 3

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Rachel's toment continues
1.7k words
4.41
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Part 3 of the 3 part series

Updated 10/31/2022
Created 10/04/2001
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This is the continuing story of my luscious girlfriend's bizarre deal with her ex-husband. In a nutshell, he would pay her one million dollars if she allowed me to punish and torture her for a year. He provided all the props, instructed me on what to do and each session was videotaped so he could verify it was done. If you haven't already done so, you really must read the first two chapters before reading this story.

In the past two days, my life has been irrevocably changed. As the result of a deal my beautiful and sexy girlfriend made with her ex-husband, I was punishing her per his instructions. What surprised and confused me was that I enjoyed it. I really got turned-on by torturing her big tits, spanking her ass and whipping her pussy. Before this began, I pictured myself as a fairly normal guy who loved normal sex. The kinkiest things I ever fantasized about was getting it on with Rachel and her sister Jamie together. Now I found I enjoyed dominating and disciplining women.

Another big surprise was that apparently Rachel enjoyed the pain. During our first two sessions, her pussy was constantly wet. And when we fucked afterwards, not only did she have multiple orgasms but she also came very hard.

I was anxiously awaiting our next session! What would that cruel bastard have me do to her luscious body tonight? Well, I wouldn't have long to wait. I hurried home after work and found a package waiting for me. The only thing it contained was a box of old fashioned, metal thumbtacks; I would guess the box contained about 100 tacks. I could only make a wild guess at what devious purpose they were going to serve. I ran inside and immediately logged into my email. His instructions were as follows:

The cunt is to wear the white tank top, the leather miniskirt and the 5" black pumps with the strap around the ankle. After your usual warm-up, I want you to blindfold her then place all the tacks close together on her dining room table. Pull up her top and have her bend over the table so her tits are above the tacks. You will then push her down onto the table and cuff her wrists to the legs on the opposite side to the table. Have her spread her legs and cuff them to the other legs of the table. Then you are to whip her ass, pussy and thighs until the are very red. Follow this by whipping her back before releasing her. Next, cuff her hands behind her head and whip her tits paying special attention to her nipples!

I called Rachel and told her the required dress code for this evening's fun, then got myself ready and went over. When she answered the door, my heart was in my throat and my cock got hard immediately. Her big, firm tits were literally spilling out of the tight top and her exquisite, long legs look superb encased in black fishnet stockings and beautifully displayed with the pumps. In spite of myself, I was going to really enjoy this evening.

"Hello Rachel, you still want to do this?" I asked hoping for an affirmative.

"Yes," she replied. "You know what I can do with the money."

"OK, go stand in front of the dining room table, legs spread with you hands linked behind your neck," I commanded.

I set up the video equipment and started recording.

I went over to my slutty, apparently submissive girlfriend and asked her if she was ready.

"Yeah, I guess," she replied.

"He has come up with a really interesting scenario for tonight," I exclaimed.

Before she could answer, I grabbed her hair, pulled her head back and kissed her roughly. My tongue began to fuck her pouty mouth. She was breathing hard when I released her.

Without allowing her to catch her breath, I grabbed both of her now hard nipples between my thumb and forefingers and pinched. She moaned loudly and pushed out her hips. I continued to twist and pull and pinch her engorged nipples and her moaning got louder and louder.

"OK slut. Turn around and pull up your top."

I went over to the implement table and retrieved the blind fold, two sets of leather cuffs, some rope and the box of tacks. I first place the blindfold over her eyes making sure she can't see a thing. Next I place cuffs on her wrist then kneel down and place cuffs on her ankles. As I rise, I can't resist caressing her tight ass and slip my finger down her crack to find her already hot and wet pussy. I linger a few seconds rubbing her clit and listening to her groan as she pushes down trying to impale herself on my finger. What a slut!

I tie lengths of rope to the legs of the table. I slide a length of rope through the D ring on one of the ankle cuffs, pull tight and cinch it off. When I repeat the process on the other ankle, her legs are drawn at least three feet apart causing her short skirt to ride up displaying the top of her stocking and just a hint of her lovely ass.

"Bend over the table and put out your hands," I commanded.

I slide a length of rope from the other side of the table through the D ring on one if the wrist cuffs and slowly pull it tight. I want to watch as she is slowly pull down onto the tacks. As I keep pulling the rope, her tits make contact with the tacks. She screams and tries to pull back. I pull the rope tight, forcing her heavy tits down hard onto the tack covered table.

"Aggghhhhhh," she cried. "Please stop. My tits feel like they are on fire."

"If you are ready to put a stop to this madness, I will let you up and it is over. Otherwise, my instructions are to whip your ass and pussy."

"I can't quit. I want the money…it is rightfully mine," she whined.

I tied down her other wrist and pulled extra tight forcing her tits down even harder into the tacks. She had forced me into this and I wanted it to end…I think.

On my way over to retrieve the leather flogger, I place my hand between her shoulders and pushed her down even hard.

"Owwwww," she screamed.

As you can imagine, bent over the way she was, her short skirt was up around her waist giving me a great view of her gaping cunt and puckered anus. I was amused to see her pussy juice leaking down her leg.

"Ah, the lady doth protest too much," I said laughingly.

I retrieved the whip and placed it in front of her lips.

"Kiss the whip slut," I demanded still amused.

"Fuck you," she spat.

I placed my hand between her shoulders again. Her tongue immediately began caressing the handle of the whip.

"Good choice!" I commented.

I go behind her and begin to whip her ass. Over and over I landed the whip. She tried very hard not to move because it would move her tits over the tacks. But as I began to target her vulnerable asshole, she couldn't remain still. Then I brought the whip down on her spread pussy and she screamed.

"Oh, please stop. My tits are hurting so much," she cried. "These things are sticking me something awful."

"You love it slut," I said and whipped her pussy again. "You are so turned-on, your cunt juice is leaking down your leg."

I whipped her pussy as few more times. Then on a whim, I ran the handle up her slit and sank it deep into her pussy. I wasn't expecting what happened next although I guess I should have. She came hard! Very hard!

After she calmed down, I brought the whip handle to her mouth.

"Suck it, slut. Taste your own juices," I commanded.

This time she didn't hesitate. She eagerly took the handle into her mouth and sucked for all she was worth.

After a few seconds, I pulled it out.

Then I raised it and brought it down hard on her back as instructed. She wasn't expecting it and again pushed her sore tits into the tacks.

After she came, I really wasn't into whipping her much anymore. I needed relief myself. I knew I wasn't going to last the entire hour. I half-heartedly whipped her back a few times. Then I released her wrists and allowed her to stand up. Several tacks remain imbedded in her tit and they had a bunch of tiny puncture marks. While I undid her ankles, she picked off the remaining tacks. Lastly, I removed the blindfold so she could see her lovely tits. Even with the pinpricks everywhere, they were beautiful.

"Alright slut, turn around and put your hands behind you neck again!" I commanded.

"Oh, no more, please!" she cried.

"Your choice," I replied callously.

I went over to the implement table and selected a leather strap to complete her torment.

As I approached, I could see in her eyes that she knew what coming next.

"Kiss it," I ordered proffering the strip of leather.

She looked me in the eye defiantly and kissed the strap.

I raised it and brought it down hard on the top of her right tit. I repeated the process on her left breast. After giving the tops, sides and bottoms are good working over, I slap her red, swollen nipples. As when we started, she pushed out her hips. I paddled her nipples until I couldn't stand it anymore.

I swiped the tacks off the table.

"Turn around and bend over the table again," I ordered.

"Oh please, I have had enough!"

"Do it NOW," I yelled.

She turned around. Spread her legs and bend over the table. My pants were down in a jiffy and my cock was buried to the hilt in her hot pussy. I pulled it out, place it up to her anus and entered her ass.

"Oh yes, that feels so good," she managed to moaned just before we both came in explosive waves of lust and pleasure.

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