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She Was A Challenge For Him, But She Was Also A Great Piece Of Ass

It's been about nine years, but whenever I go north on a business trip, I look back on some of the best sex I ever had--a conquest close to getting that virgin cheerleader back in high school.

I was a midlevel administrator in a large public-sector operation that hired many women who traveled for a week or two at a time, conducting training sessions or supervising completed work. I made shorter support trips to the places they were working. I have long contended that women who travel, leaving their husbands and children behind, can nearly always be fucked. Different women have different buttons to push, but find the right one and you will get laid.

With two guys in similar positions, I had developed an interesting bet some years earlier. We each wrote the names of two women employees on slips of paper. Then we mixed the six names in a bowl and each drew one. If you could fuck the woman whose name you drew within six months, you won two hundred fifty dollars from each of the other guys. (Since the women didn't report to us, we didn't have any benefit of undue "influence.") If we all scored, the bet was a tie--no one won any money, but we'd all gotten some "strange pussy." Most times two or all three of us got laid. We had had this bet for several years, and never had everyone been shut out.

We were careful about the names we put in the bowl. Rule one was to make them women you'd like to fuck, because you might draw your own nominee. Rule two was that they had to be married. Housewives don't tell, plus it's clean pussy. The greatest sex in the world is out there wearing someone else's wedding ring--these women have spread their legs for years, and the only ones getting off are their husbands. Sometimes I think women need "strange stuff" more than men do. It's my pleasure to help them realize that.

The time in question, I drew Dory's name. It was the third time I had put it in the bowl, but no one had ever drawn it. Dory was about forty, had three kids, lived in a small town, put everything she had into her job and was always cooperative. If she would cooperate with me, I would put everything I had into her! She wasn't a flat-belly, but she had a pretty face, breathtaking tits, perfect legs and a look about her that she could fuck all night long. And she had always been friendly to me. This was one bet I felt confident about winning.

"I was so hot, but I didn't want to come right away. I took to visualizing college math formulas. I really wanted this first time with Dory to last"

For such a small woman, Mistress Roseanne generates a lot of power, and soon I was in ecstatic agony, my cock dripping like a faucet. She put a condom over it and then found some nipple clamps among her toys and tried to see just how tight she could make them. I winced as she turned the screws, bolts of electricity shooting from my nipples through my chest. Once they were in place, she ran a vibrator over them and my bound genitals. Talk about mixing pleasure with pain! My whole body was alive and I writhed within my bonds. Loosening my bonds, she set me free and then made me put on a pair of pink satin panties.

We conducted our professional day and went out for dinner. After eating, we chatted and I had a few drinks. Dory didn't drink--there went that inhibition-easer! Oftentimes on these bets the "strange" knees were first spread after relaxing in the bar, either celebrating a successful day or trying to ease the pain of a bad one. Still, we had a nice time talking, and I felt Dory was being especially friendly. After some time we walked back to our rooms. The supplies were in my room, so we transferred what she needed to hers.

Dory had her back to me, shuffling through some papers. Hoping I had read her friendliness correctly, I came up behind her, kissed her neck and cupped her 36C breasts in my hands. She didn't stop me, but said that she was married and couldn't do anything more. We talked and necked for about an hour. She said that she was really attracted to me, but couldn't do what we probably both wanted to do.

Realizing that pushing the issue would do no good, I said I respected her wishes and hoped she wasn't offended but I found her very attractive. She smiled and appeared pleased. I saw I was going no further, so I took my hard-on through the adjoining door to my room and went to bed. For a while I hoped there would be a knock at the door, and then Dory naked and primed for a bucking. But that didn't happen.

The next day we conducted our business, with no mention of the events of the night before. After work Dory asked if I'd like to go dancing in a town farther from her home, so no one could see us. Sounded great to me! Since I'd flown in and she had her car, she drove the hour trip. Nice conversation. She said her husband didn't like to dance, so she had no chance to perfect her skills. We had a nice time stumbling around the dance floor, and when she suggested we go back to the motel, I was more than ready. I hoped she had changed her mind about sex. I fantasized about coming in this shy housewife's box.

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