| Straight: BDSM: A New Era (3/10) |
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and fuck her consensually, no lessons for one year.” “And if I fail?” “Oh, the usual, but now you will have to actively agree with me every time I tell you how inadequate you are.” “One last question. Do I have to go in cold, or can I use the Internet, personal ads, etc to find a potential date.” “Sure, little boy. Use whatever you like. You’re a sissy, and any woman can tell it. The only thing I want is proof that it actually happened. I’ve got a little pocket tape recorder you can carry to collect the evidence. And just to make the challenge legitimate, you can’t abandon your sissy underwear until you actually get someone in the bed. That will be a little tricky, but I’m sure you can manage it.” It sounded like an easy bet to win given the lack of restrictions, so I got busy on the net, and within the day had struck up a email conversation with not one, but two, women who were looking for a man 40-45 to play with together. They specified “single, divorced, or separated,” so I chose the latter. I figured it was okay for a one-night stand. I responded to their ad, we qualified each other for fit, and then went far enough to know we were all interested. We swapped phone numbers, did the verification thing, and then exchanged pictures. Karen was a little chubby, but she and Diane were both descent looking and sounded fun, so we started looking for a time to meet. In the meantime, we were having fun with email chat back and forth about all the things we enjoyed sexually. Mistress Anne was of course demanding regular updates, which I provided with a gloat. She insisted I call them from her house a couple of times just to “see if this is real.” There was a week coming up when Joyce was going to be traveling on business Monday-Wednesday (this week), so Mistress Anne pressed me to prove I could do it by setting up a meeting. We picked Wednesday, agreed on a bar, and all was set. The underwear thing concerned me just a little, but since this wasn’t going to be romance… just sex… there wouldn’t be any hugging or kissing, and I could just strip in the bathroom and put on a robe. Mistress Anne, sensing defeat, then sprung one additional condition - I had to wear a bra and panties to the bar under my clothes. I of course said, “Are you kidding - when they see that - they will run the other way.” “Don’t be silly - I don’t expect you to let them see it. You can go to the bathroom as soon as you get them home or to a hotel and take them off. I just think it’s only fair you prove you can do it while you are dressed like you always dress.” Feeling pretty confident, I said, “OK.” So here I was in a bar two nights ago on my third drink with Karen and Diane. Mistress Anne had made me stop at her house on the way to make sure I was dressed as expected. Karen and Diane’s pictures had been flattering. They were not nearly so attractive in person. There were two hot looking ladies standing 5 feet farther down the bar, but hey, I wasn’t going to be choosy, I just wanted to win the bet. I had the tape |
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Great Job
