Chapter One -- Rick Takes A Chance
"That's it?" she asked. "You want me to embarrass you?"
I attempted to read her voice for judgments or incredulity, but neither was there. It was more matter-of-fact, as if she were asking for clarity, to make sure she understood.
"Yes," I answered. This was the tricky part. Rachel was a good friend, what the young people today would call a friend with benefits. She and I had been dating for a couple of years. Neither of us wanted to get married again. We were both in our Fifties and in reasonable shape for our ages. I'm no hunk at 53, but I'm not ugly either. I find Rachel attractive at 55, though I know she has a few (not many) more pounds than she did 30 years ago. She's in good shape. And we've both been sexually adventurous in our lives, both before and after we met.
Rachel broke the silence that followed my 'yes' answer. "What do you mean by being embarrassed?"
I shifted in my chair. We were sitting in her breakfast nook. It was late at night and we'd just finished a nice lovemaking session and were taking a break with a glass of wine and some leftover pizza.
"I'm a little embarrassed just to say it, but that's not exactly what I mean. For as long as I can remember, I've wanted to be compelled by someone else to do things that would embarrass me."
"Like what?" she asked. She leaned forward and took a slice of pepperoni and some attached cheese from the leavings on the platter. She looked interested.
"Like having to undress wherever I am or having to wear a stuffed bra under my shirt so that it's obvious I'm a guy wearing a bra in public or having to allow someone to have sex with me whenever or wherever they want or to have sex with someone they loaned me out to or having to hold my urine until I'm bursting then having to pee myself publicly."
I stopped. I tried to make my statements matter of fact, but I could feel myself blushing, and I had to look away in embarrassment. Mostly, I needed to hear some feedback from Rachel. Had I turned her off the idea or, perhaps turned her on? I could feel that I was quite erect myself, but she couldn't see it.
She chewed her pepperoni and cheese, swallowed, and took a sip of wine. "Stand up," she said. I stood. Given that I was wearing a loose robe that wasn't tied, as was Rachel, as soon as I stood my erection was apparent. "Well," she said with a slight smile, "you're certainly turned on by the idea," with a nod to my cock.
"Sit back down, Rick. I have some more questions." I sat.
"How do I compel you to do something that you don't want to do. I mean lots of people have fantasies and daydreams. That doesn't mean that at the drop of a hat they'll indulge themselves. If, for example, I told you to pee yourself in public, what would compel you to do as I said? I'm not strong enough to make you. Besides, others might intervene if they thought I was manhandling you."
I didn't have to take time to answer this one. "I had that question myself for a long time, which is why it stayed a fantasy. But recently I read a story series on the Internet about a woman who did a contract with a guy to use her like a slut. She wanted it, and he was interested. But he asked the same question you did. Her solution was to give him blackmail material to use on her if she chickened out. We could work out something similar to ensure that I followed through on this."
"Rick, honey, I don't want to blackmail you. I don't want to ruin you in the community. That would be cruel."
"Rachel, I don't want to be ruined, as you put it. I want to do this. I have a whole list of things back at my place that I want to do but that I've been kind of chicken to do. For years I've just put them aside as some things I would try if I got the chance but either they never came up or I passed on the opportunities when they offered. I chickened out. But they won't go away, and I want to do them. I need to be responsible to someone else, accountable to them. I'm sure that if I gave you some compromising photos of me, or you took some yourself, and you had to threat of releasing them to my email address list if I didn't follow through, just the threat would be enough to make me do what I was told to do."
Rachel sat back in her chair, obviously thinking. After a long minute, she said, "Be a dear and get me some wine," holding up her glass. I took it to the fridge. "Take that robe off for me, Rick. I like to look." I set the glass down and shrugged off the robe. Yes, I was still hard. Then I took the bottle out of the fridge, filled her glass and brought both glass and bottle back to the table.
I gave her the glass and started to refill my own when she put a hand out and grabbed my cock. "Just set the bottle down, Rick and stand facing me with your hands behind your back and your legs spread." I was surprised, but I did as she said. I stood there looking at her while she looked me up and down slowly as if seeing me for the first time, or at least in a new light. I began to find her gaze and my position, standing naked and open to her with my cock bobbing ever so slightly embarrassing. I was glad she had me hold my hands behind my back, because I was having this urge to cover my erection.
Her gaze apparently took all this in. "You're embarrassed, aren't you?"
I felt my face flush. "Yes, ma'am."
She smiled. "Ma'am? I like that, but then you have always been a polite boy." I found myself feeling more and more embarrassed, and I felt my cock getting harder and harder.
She continued to sip her wine and look at me. At one point, I looked away; the staring was making me more uncomfortable. "No, no, my pet. Look at me. Look at me and think about all of the humiliating and embarrassing things I could do to you."
God but this was embarrassing. She wasn't doing anything provocative, just sitting there, examining me and sipping her wine, like she was at an art show appreciatively regarding a sculpture. I felt mesmerized by her gaze, and I realized that she could make my wildest fantasies come true. I also realized that she might possibly have me do things I hadn't thought of doing or had shied away from in my own imaginings.
After some time of this, Rachel seemed to make up her mind about it all. "Come with me," she said, putting down her wine glass. She rose, and without a backward glance to see if I was following, walked through the living room and into her study. I followed keeping my hands clasped behind my back.
Once in her study, she opened a desk drawer and rummaged in her purse, pulling out her cell phone/camera. "I'm going to take some pictures of you to use as blackmail material. If you agree, then I'll play your game, and we'll see how far you'll go with it."
I stood still in the open door. "I agree, ma'am."
She looked at me for a few more seconds, as if giving me a chance to back out. When I didn't, she calmly pointed the camera and shot off a flash picture, which she then examined. "That's a keeper," she said. "Now, take a hand and stroke yourself lightly while I take another picture." Soon the flash went off again.
Satisfied with this second picture, she had me stop while she sat down at her computer and powered it up. Shortly, I saw her downloading her pictures from the camera and looking at them critically on the screen. "Good," she said as she closed up the picture folder, "those will do for a start."
She turned back to me with camera still in hand. "I'm creating a blackmail file on you that I will use if I have to. Now, masturbate for me and catch all of your cum when you orgasm. I don't want anything on my carpet. I just had it cleaned."
Wow. That was my first thought. She was going to do this. I suddenly felt a little queasy even as I reached for my cock to do as she wished. This had gotten very real very quickly.
She stopped me as I started to stroke. "Wait, you haven't thanked me. You must always thank me for whatever task I give you."
"Thank you, ma'am," I said numbly.
"Good. And you must always address me as 'Ma'am.' I find I like that."
