SATURDAY

I'm not proud of it but I fell in love with one of my wife's friends, after I saw her in a very sexy picture. Her friend never got married but she's had this boyfriend now for about a year, and she's dressing much sexier than I ever remember.

We don't meet very often, maybe once a year, as she lives a six hour drive away. Plus, she's often in Vegas now, as her boyfriend is a “professional” gambler.

And she would be there as well while I was visiting a conference for my company. A perfectly good reason to meet up with her, right?

The conference was from Tuesday through Thursday, but I flew in on Saturday already, for a nine day visit, so including some personal fun. And Saturday night I would meet Angel and her boyfriend in the casino of the hotel where I stayed, and where the conference was.

I hoped she'd be wearing the sexy leather dress that I had seen her wear in the picture my wife had shown me. Both women knew from early on that I liked leather, but it was just not something they'd wear. So, I figured the boyfriend had to have something to do with it.

When I met them I knew I was right, though she wasn't wearing the dress I had hoped. Instead it was even more beautiful, an evening gown, in the softest leather. I knew I hugged her too long, but my hands felt so good on her leather.

The boyfriend, Jaxon, was slick, much better dressed than me, but his only interest was in roulette and blackjack and stuff. And soon he dismissed Angel, telling her to show me around. I didn't realize that to her it meant we went straight to her hotel room.

Long story short, she had always been jealous of my wife, apparently both of them had had their eyes on me, when I started dating Sonya. It was one of the reasons that Angel had moved away.

Now, her current boyfriend had a need for a trophy wife/girlfriend. Someone sexy, that could distract perhaps his opponents, even if it was for just a few seconds. Angel could therefore spend a lot of money on clothing, but he insisted it was always leather. And that way she had grown fond of herself, even addicted to the material. And she confessed how she finally understood my desires that my wife always had laughed about with her.

And now that she had me in her room, she wanted my hands on her leather again. And much more. Like catching up on what she had missed all these years I was married to her best friend. When I protested that my wife would find out, she promised that what happened in Vegas would stay in Vegas.

I wish I could say I was stronger and more faithful, but it was a dream come true. I had always admired her shiny dark skin and her womanly curves and long legs. And as she pulled her skirt up a bit, she sat on her hands and knees on the bed, and she told me to put my hands on her leather hips.

Her pussy was dripping and she simply told me to fill her up. I was so hard that it was a relief to get it out of my pants, and within seconds I had mounted her.

Again, I wondered what I had been thinking all these years ago. My wife only likes the standard position, on her back, no oral, no sixty-nine, no doggie style, not me on my back as she mounts me. And Angel liked all of that.

She was not upset about me shooting my load as quickly as it happened. But she made it clear that she wanted more. I had to make her cum as well. And for that, she wanted me to wear some of her leather. She simply could not cum without it.

I had never really had any desire to wear female clothing, but when she pulled the dress I had seen in the picture from her closet, I couldn't resist. And in minutes I realized that feeling leather on your own skin, and her hands on mine, was even better. What had I started?

It wasn't perfect though, as the dress had room for her significant buste, where I had nothing. But she had a solution, and she pulled some breast forms from a drawer, and the fit was now much better, the cups perfectly filled. I was surprised by the weight, as I held “my breasts” in each hand, and it felt just like I had felt her rack in my hands, minutes before. So my manhood came alive again.

Obviously my curves were not as good as hers, but the bump showing in my crotch area was not fitting. Again Angel had a solution, although I didn't appreciate the ice cube she pushed in my crotch. But it shrunk me down, and then she pushed a rubbery sleeve over it, that locked behind my scrotum, bending my manhood between my legs, and when she pulled my skirt down, no bump was visible. She pushed a tiny key in my hand, warning me not to lose it, or I would have trouble ever cumming again.

Next thing I know we're in a sixty-nine position and my tongue in her still soaking pussy, that I had filled up as well. It didn't taste too bad, as her own juices were overwhelming, and I wanted to return the pleasure to her. At the same time her hands were on my leather hips, my butt, my breasts, and she licked my crotch through the leather. The thing she had put around my dick stopped me from growing, so I concentrated just on her pleasure.

I was rewarded finally with a wave of her juice, mixed with my own cum, and as I didn't want her beautiful gown to be ruined, I sucked it all in. And had to swallow multiple times. That's when I heard someone applaud.

It was Jaxon and we were caught red-handed. But he didn't seem upset at all, because Angel told him she'd put a chastity device on me, so I couldn't fuck her. Not quite the truth, but as I had just eaten the only evidence of wrongdoing, I simply nodded.

He wanted to see my crotch, so I pulled up my skirt, and next thing I knew he had added an additional ring around my scrotum. “Let's see if this works”, he said. He had a small remote control in his hand, and pushed a button.

It was as if my balls were on fire, the pain in my crotch shutting out everything else. As I cried out he pushed another button and the pain stopped. Before I could protest he pushed a new button resulting in a pleasant feeling that made me forget the pain. It was like a slight vibration that increased when he moved a slide.

I couldn't call it a hand or a blow job, but the pleasure increased rapidly. However, it caused my dick to grow, and there was no room for that. The pleasure turned into discomfort real quickly, and it got worse and worse.

Soon I cried out again to stop, and so he did. Then the pain started again, which reduced my erection right away, but the same slide controlled the amount of pain as well. This went back and forth a few times between excruciating pain to impossible discomfort due to the pleasure applied, and I begged him to stop. He told me, only if I gave him my key.

I looked at the key in my hand, and he warned me that if I gave him the key, it would be his decision to unlock me or not. And lock me again. I held the key back, not willing to give up on my potential orgasms, but after two more pain cycles I gave up and handed it to him.

He didn't take it right away but told me to say that I put my rights for any orgasm in his hands, and so I did. Finally the pain stopped, as tears ran down my cheeks. “Very well”, he said, and he complimented Angel on preparing me for him so well. Tears were also running from her eyes, as she muttered, “My pleasure, Master.”

Master?

He ordered me to sit doggy style now, and punished me with more pain when I didn't move fast enough. Then he ordered Angel to lube me up, and as she lifted my skirt and rubbed some cool gel in my anus, he motioned her out of the way, and he pushed his hard dick deep inside me.

I cried out again in pain and shock, but he used his remote to give me just enough pleasure around my scrotum, to compensate for the discomfort in my rear. He started pumping me, touching something inside me that increased the pleasure in my crotch. I couldn't help it but I started moaning, and soon after he shot his load inside me.

When he pulled out, he ordered Angel to plug me up, and she pushed something in my still gaping hole, which kept the cum inside me. Then he ordered me to stand up, as he looked me over with piercing eyes.

It was very simple really. I was to be his prize possession for the week, and as long as I did exactly as he or Angel said, he would consider freeing my manhood, just before my flight home, and my wife would never find out. I was to dress in anything that Angel provided, and to sleep in their bed every night. I would be Deanna, rather than Dean, and participate in any sexual act they wanted.

But what about my conference? People would question where I was?

He wanted my driver's license, and said he would take care of it. I would participate as Deanna. That scared me more than anything he'd said before, but Angel promised she'd help me through, and that I would find out that making deals as a sexy woman was way easier than for a “boring” man. I sort of believed that, but I was hardly a sexy woman…

Jaxon had a solution for that, as he knew the owner of the salon here in the hotel, and when he called to make an appointment for me the next day, I was told I could come right away. This was going much quicker than I could handle, but I knew I was at their mercy. So I started taking the dress off, in order to put my own clothes on, but Jaxon stopped me. I was Deanna now, and go as Deanna.

Angel helped me with a wig, and some makeup, and although I thought I looked like a guy in drag, I made it to the salon without a second look from anyone. Vegas is used to much more extreme.

The lady at the salon, Cynthia, was very nice and she promised that even I would not believe that I wasn't a woman. But it would take all night, and she told Angel to provide clothes for me in the morning, as I took off my dress and wig and breast forms and even my wedding ring, before soaking in a hot bath in the back. It was very relaxing and the fumes almost put me to sleep, but my skin started burning, and Cynthia told me to get in the shower and wash my face and hair.

My skin soon felt better but I realized all my body hair was gone, and I was glad now that I hadn't submerged in the tub, which I had considered. The shampoo was nice, very flowery smelling, and much thicker than I'd ever used as a man.

Cynthia patted me dry, as my skin was very sensitive, and she had me lay down on a massage table, all naked except for my chastity device, as she covered me with a sheet. My hair would be done first. It took forever and was sometimes painful. She gave me something to chew on and I soon felt myself doze off.

The few times I woke up she had me chew more of the “candy” and I was only distantly aware of what was going on. After my hair she worked on my face, my skin, my nails, my waist, my chest and my crotch area. Sometimes it would hurt, but she'd give me stronger candy.