A dare becomes an obsession - Sex Stories

A dare becomes an obsession

... used her tongue to lick his asshole and all along his crack. Jill pushed her face in deep and inhaled the fetid aroma of a man who probably had not bathed or used toilet paper in months. I almost wretched as I watched her lick and suck him. She reached around and began to stroke his throbbing member as her tongue was still buried in his ass.

Jan, then got into the action and plopped down in front of the guy and started sucking his dick. In just seconds the guy blew his load in Jan’s waiting mouth. Jill spun him around and sucked the remnants of his cum from his softening dick.

Both ladies were all smiles from the decadent act. Jill stood up and started to kiss the homeless guy but he would have none of it. He was not about to kiss a woman on the mouth that had just rimmed his asshole. Jill was a bit miffed but got dressed and collected her one-dollar winnings from my wife. As Jan gave her the dollar she leaned in and passionately kissed Jill and licked her face. It was incredible to witness.

I presumed this was the last of these crazy dares, since it just could not get any dirtier, than what we had just witnessed. But as we drove home after this event, both girls were enthusiastically brainstorming what other vile acts they could perform. Jill’s husband and I were both still in shock and could not believe they had more perversions yet to experience.

The last of these events, which just happened a few weekends ago, was to be the craziest idea yet. But neither ...

... Jill’s husband nor I had been told what the girls were planning. We went to a bar to have a few drinks which was not far from the same downtown area where several homeless men gathered. The girls, by this time, felt completely comfortable with their little scenario of approaching a group and making their proposition. This time it was Jan’s turn to take the dare. And this is where I failed as a husband. I let my voyeurism control my good sense and let this happen.

This last dare was for Jan to have sex with one of the homeless men. To let him penetrate her cunt but not wearing any protection. No rubber. I just knew this really could not happen. Jan would get up close to the line but balk at actually allowing a homeless man to fuck her bare cunt. This was too far out of the realm of sensibility, even for these two ladies. My heart was pounding in my chest as we approached a group of street men.

Both Jill and Jan casually approached them. There were a few men that we recognized from previous encounters, so they pretty much knew something interesting was going to happen. Jill’s husband and I stayed in the shadows, and did not want to impede this, but the truth is that I did not know what to say anyway. Could I demand that Jan not go thru with it, even though I was confident that she wouldn’t anyway? I did not want to be the killjoy of this prurient activity, but I also did not want it to occur. I was torn with indecision, so I did nothing.

I could not hear their conversation ...