The Dare

byTheChameleon©

Like every morning, when I get to work, the first thing is to open my e-mail, always anticipating a letter from Val.

It had been that way since she had moved away, it went from flirting at work, to having a sexual work relationship and eventually being an affair.

Through it all, we had remained best friends, always looking out and after each other, yet always pushing the limits of the other.

A strange, yet satisfying relationship for both involved.

My heart skipped and I got hard instantly as soon as I seen a couple from her, she was also the best at cybersex, phone sex, in fact it was her that initiated me into all of this, and I loved her for it.

Calling her my soul mate would be an understatement.

I opened up the first e-mail, and it said, how was your weekend Hon, get any?

Just like her, she knew that my wife and I rarely fucked, let alone had intimate sex.

She has never been into it, oh sure, when we were dating, she acted like a horny slut, always talked about eventually being experimental, but that died right after the vows.

She then went on to tell me about fucking her husband in the shower, how he was getting a little older and needed some help, sometimes a pill, sometimes a little kinky. This weekend was kink, and she loves it, she went on to describe sucking his cock in the shower, before letting him fuck her in the ass, the one sure thing that still got him hard. Of course I could relate, because damn, she loved to have hard cock in the ass, and I loved doing it her as well.

Then I read the next letter, and it was simply this, want to have some fun at work this week, let's play dare!!!

She said, I get to dare you to do something at work, and you get to dare me, we will see who backs out first.

We had played this game before, as we both love taking chances, the thrill of getting caught.

Once she went into the men's bathroom, stripped down and pissed in the urinal, she had me sit at my desk, in a shared office, while she sat beside me, pretending to do a web seminar, while my coworkers worked away, oblivious to the fact she had my cock out and was jerking me off.

So, of course I replied yes to her latest offer.

A few minutes passed and I received her next e-mail, and she said that she wanted me to seduce a friend of ours at work. Actually more like her friend, I admit she had told me about her before, but I did not really know her.

She went on how this friend was single, had been screwing a few married guys, but they only cared about getting off, and she was fed up with guys like that.

She said, she knew I loved sex, and that the best part was watching a woman get off, get lost in her pleasures. She knew that for me to get off, it has to be more about reaching in to another person, finding out what dark fantasies they have and hopefully helping them live them.

And she also knew with me, the more perverse the better, the idea of corrupting an innocent or bringing a vanilla virgin to the dark side, well, that was my fantasy and she knew it.

She told me that Gail had sworn off men, but if I was up for the challenge, maybe we could have her rethink this.

God, I love this woman, she knew what I would like.

I e-mailed back, and asked for a picture Gail, and within minutes, it arrived.

She was a little different than I anticipated; for one she was older, mid-fifties, a little larger, yet not really fat and a little plainer, yet attractive.

Still, I definitely would enjoy this dare, yet not sure if I could pull it off, after all she had sworn off married men, and I was definitely one. And for me to seduce, I always prefer to be honest, that makes the challenge better, and of course lets the woman no, that there are no strings attached, and like a buddy once told me, be blunt and honest, sometimes you get a no, sometimes a slap, but the one time out of ten, your fucking doors will be blown off, and he had been prove to be right for the most part.

Over the next few weeks, I would send jokes, always cc'ing Gail, and as our replies went back and forth, Gail eventually started joining in. Definitely a good sign.

Soon the next step, I started sending a few flirtatious and suggestive jokes to just Gail, gaining some trust.

Soon she was flirting , and I wanted to have her believe that she was the one now initiating it, and so I backed off the e-mails, and sure enough, I got one asking if I was losing interest in her.

I waited a bit and then replied, No way, I just wasn't sure how you felt, and I do not want to offend or hurt you.

I think that did it, and she seen me more as a friend, and she started to confide in me.

I was building confidence we would be able to pull this off.

Another week of suggestive flirting, and I sent her a picture of me stroking my hard cock at work, and her reply came back. WOW, you are not really doing that at work?

I said, I sure am, and I am thinking of you as I do it.

I then asked her, if Val had ever told her about me. She said yes, that she was told we had an affair, but she did not go into details.

I told her about my marriage, how Val had seduced me, of course not like I was not willing.

As we talked back and forth, I told her that I would love to go down on her, to taste her lips, etc...

The usual plain stuff and she always wrote back that she liked it

Soon it was time for the next step, to introduce some kink.

I started telling her how I would love to stretch her tits, to make her nipples so hard, they pinged. To bit e them, and to slap her "fat" ass

To my surprise, she got into it quicker than I thought, she said no one had talked to her like that before, and that it was making her pussy wet.

I replied, it is making your what wet? I am sure you meant cunt right?

She wrote back, YES, you are making my cunt wet!!!

I think you would make a great slut, getting bolder, I think I would love to fuck your mouth, not a blowjob where you suck me, but where I actually fuck your mouth.

The more I wrote, the hotter she would get

Soon I had her masturbating while we exchanged e-mails

We talked about whipping her tits, clamping her nipples, and even having her holding my cock as I pissed.

She seemed to love it all.

Well, I decided now or never, and asked to meet her for a drink, and of course she accepted.

We met at a bar where I used to frequent with Val, and with an hour we were off to her place.

Once inside, I grabbed her, and kissed her deeply, tasting her tongue, gently biting her lower lip, caressing her sides.

As she sunk further into my arms, I asked her, are you sure you are ready to be my slut?

Yes!!!, I said , I mean a real slut, try anything.

She just looked at me and said anything!!! Just fuck me!

We walked into the living room, I sat down and told her to stand back and take her blouse off. She looked nervous but complied and a soon she was standing there, wearing a powder blue lace bra, her large freckled tits spilling over the top.

Now the bra, I said matter of fact, and she removed it, exposing her large nipples, not so much long, but very wide. Begging to be stretched and tugged, I stood up and grabbed them roughly, pulling the nipples as far as they would go, and then releasing them to watch her fat tits bounce. She just rolled her eyes and let out a throaty growl. Here was a woman that loves sex, rough sex and no one had ever figured it out.

And it amazed me.

I lifted her tits, just to feel the weight of them, heavy firm, made for playing with.

Bite your nipples I commanded, as I lifted them towards her face.

She strained forward and began sucking on one.

I dropped it, and looked her in the eye, and said, I told you to bite them, not suck them.

I am sorry she replied, and I then said, Lift those tits, and bite them

She lifted the left one and took the nipple between her teeth and I reminded her, I expected her to chew down on them until it hurt, as she moaned, I told her to do the right one.

Next I had her remove her skirt, and turn around.

I slapped her and asked how her fat as liked it (She knew I was just saying it was fat for effect and was not really insulting her)

She said she loved the stinging feeling

I reached into her panties and could feel the meaty folds of her cunt, which was already starting to leak juices.

Her clit was larger than I had ever seen before and I wanted to suck it into my mouth so badly, but if I was to succeed in turning her into a special submissive slut, that would have to wait.

Next I had her remove her panties and bend over resting her arms on the end of the couch.

I came up behind her, spread her ass cheeks and ran my tongue over her wrinkled anus.

She jumped a bit and said, no please, no one touches me there.

I said, no one used to, but I guarantee you, from now on, I will, and I am sure you will enjoy it.

Again, I ran my tongue over it, and started to push my tongue inside, tasting her virgin musky hole for the first time.

There is something special about a virgin asshole, the taste is so nasty.

I turned her around, put my hands on her shoulder and started to push her to her knees, knowing what I expected; she undid my belt, button and unzipped me. Taking my cock out, dripping with pre-cum, she stuck her tongue out, looking up as she lapped at the strands, not missing a drop. Soon she was taking it in her mouth sliding her lips up and down the length, each time taking more and more. Soon she had her nose right in my pubic hair.

Soon I grabbed her hair, and gave a little tug, and she released my cock from the warm wet confines of her mouth, I tapped my cock against her cheeks, spraying her with a mixture of her saliva and my cock juice.

I sat in the armchair, and lifted my legs, and told her to clean my balls real good.

I used to shave them, but I have noticed that a lot of the real nasty sluts like to lick hairy ones, so I have let it grow back in.

Soon she was licking and sucking them as if she had not had a meal in ages. Now was the time to push further, and I guided her head down to my brown hole

She hesitated a bit, but she must have decided on her won to go forward, because I felt her tongue lapping at the hole licking my hairs, and soon probing inside, pushing her self deeper and deeper.

It was if, she had discovered a new treat, she was tasting my shit hole as if there was no tomorrow.

Now normally I only like the feeling of power when a woman rims me, but hell, she was so enthusiastic, I grabbed my cock and started to jerk while she tongued me.

Knowing I would not last much longer, I had her stand up, and turn around. I had her bend forward and positioned my cock at the entrance to her now dripping cunt, and entered her. It must have been awhile for her, because her cunt started to clamp on me, and actually draw me into her.

I kneaded her ass as I slowly started to fuck her, then grabbed her hips and started to ram her harder and faster, her matching me stroke for stroke. She started to moan, and I knew she was cumming, her legs started to vibrate and she screamed out something, but I could not make any sense of it, like an animal, wailing.

I reached around her and grabbed those heavy swinging tits of hers and I pulled and stretched and slapped them. The more I abused her, the wilder she became.

I pulled back a bit, as grabbed her ass cheeks, pulling them apart to stare at that virgin back door, and I knew I was going to have to have that too.

I spit on my fingers and coated her hole, and slowly pushed one finger in, feeling my cock rubbing it through the membranes.

As she relaxed, I introduced a second finger, going slowly. She tensed up as I put a third finger in, so I rubbed her back, and talked to her, telling her to relax, to breath slowly, and soon she was fucking my cock again, as I fingered her ass.

I told her it was time to fuck her virgin hole and asked what she had for lube.

She told me all she had was conditioner for her hair, and I ordered her to go get it.

When she returned, she looked at me nervously, but I re-assured her, I would not hurt her, in fact, I promised to stop if she said so.

She got on her knees and elbows and presented me with that fine ass, and I generously coated her asshole, and positioned my cock at the entrance.

As I began to enter, I felt her tighten up, so I leaned forward, and gently rubbed her between her shoulder blades, calming her, and I pushed deeper, al the while letting her know, it was slow and easy.

Once I was fully in that warm dark tunnel, I asked her how she was doing, and she said uncomfortable, but not as bad as she thought.

I slowly started to fuck her and soon she was meeting me, urging me to fuck her ass.

I was getting close to blowing my load, and I told her to rub her clit.

Soon we were both groaning and cumming, and we collapsed on the floor, and my cock left her ass with a plop.

As we gathered our composure, she looked at me with a smile, and asked when s my next visit to my newly anointed slut was going to be.

Over the next week, both Val and I confided to Gail about the Dare.

Once she got over her shock, she thanked us, and we are now planning a trip to see Val., where Gail will experience her first taste of Sapphic love.

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