A dare becomes an obsession - Sex Stories

A dare becomes an obsession

... things that other beautiful young married women would normally never do. Jill dared my wife Jan to pick up a homeless man once and see if she could get him naked. This poor guy did not understand what was happening, but stripped down an alley, with the hope that he would see her naked too. He was standing there in the dim light, buck naked, waiting for her to strip down too. She just laughed, took his photo, and ran off. She won her one dollar bet with Jill.

The idea of fucking around with homeless men became a common theme with these two. Jan dared Jill to suck a homeless guy’s dick. Jill took the bet, and they easily found a street guy who was willing to be flirted with by two beautiful girls. He may have been homeless and dirty, but he was not stupid. He played along. Jill told him her girlfriend wanted to see her suck him off. He found a quiet spot away from any witnesses and pulled off his pants and underwear. Jill squatted in front of him and grabbed his filthy penis. She pulled on it to get his blood flowing, and I would be damned if she didn’t start sucking him off. The guy was astonished. He grabbed her head and began face fucking Jill. I don’t know if she had planned to have him take control, but he soon was shooting a load of spunk into her mouth. She swallowed his load and continued to suck him clean. She popped up from in front of him, wiped her mouth off and thanked him for his participation. Jan handed her the dollar to pay the bet, and the girls giggled ...

... and trotted off back to the busy street.

Another evening and another excursion with them looking for a homeless dude happened a few weeks after Jill sucked that guy off. It was Jan’s turn to do a decadent act. She approached two or three street men in another dark alleyway. The bet this time was for her to let them cum on her face and she had to wear their cum for the rest of the evening. I was shocked that Jan took this dare. Me and Jill’s hubby were always away from the action in the past, but this time I needed to be right there to witness it for myself.

Jan told the guys some story that she had an unusual attraction for men living on the street. She told them what she wanted. She would suck them off, as a group, and when they had all been serviced by her, they would surround her and shoot their cum on her face. She could not get them to believe this was not some kind of trap, so she had to strip down to prove she was serious. She slowly pulled off her shirt, then her bra and handed them to me. She kept going. She shimmied out of her shorts and pulled off her thong and was naked to the world. I took those clothes from her too and she said “there, now do you believe me?”. The men dropped their pants and presented their growing erections to her for servicing.

I was astonished. To think that my lovely young wife was really going to do this was incredible. I could not find words to say. I was dumbstruck and just stood there, like a butler, holding her clothes. She ...