I couldn't help but look at the woman who crossed our path near the pool at the hotel where we were vacationing. It was approaching evening and she was wearing a long, form fitting, shimmering white dress, and only the large head cover hanging on her back made me wonder if this was a beach dress rather than an evening dress. And she heard me when I told my wife what a beautiful dress it was.

She stopped, and turned back, looking at my wife, and she asked her if she liked the dress too. I had a feeling about what my wife was thinking. Both women were black and both gorgeous, even though my wife never thought she herself was beautiful, especially not next to this top model.

But, she agreed with me that the dress was gorgeous, and then asked if it felt as good wearing as it looked. At which the model replied, why not try it out. Her husband had bought the dress for her but it was a size too small, so she had bought a bigger size, but it seemed that my wife would fit the smaller dress perfectly.

And just like that the two disappeared, after the model told a man who was guarding a private stairway, to “take me up” to her husband and wait for the two of them to come back.

The stairs led to a totally private area with its own pool, bar and outdoor kitchen. I realized that not one room in the hotel had a view of this private area. I had no clue this was even existing.

The husband, a large black man in an expensive bathrobe, was clearly very wealthy, and listened to the man who brought me up, then came to me with his hand stretched out. His grip was strong but friendly, as he invited me into his cabana.

We laughed about our wives, so easily distracted by beautiful dresses, and I kept my mouth shut about being distracted first. But, he hoped that maybe this led to our wives becoming friends, as his wife didn't easily make new friends.

I hoped so too, but it was soon clear that between him and me we didn't have a lot of matching interests. He was into gambling, having lost about fifty grand the night before, where I was worrying about my investment of about five grand, that I had been building over the past years.

He drank hard liquor, while I did a beer, maybe a glass of wine at best. He smoked expensive Cuban cigars, while I smoked… never. He wore Armani suits, while my one suit was bought at Walmart.

The only thing we shared was the love for our wives, and being amazed at how good they could look. He found out I was saving some money to buy her a leather dress, real leather, and he told me his wife had a few.

Things turned awkward when he asked if I would ogle his wife, if she'd wear a leather dress, and I tried to laugh it off. But the thought of his model wife in such a sexy dress made my dick grow in my swimwear, and it was clearly noticeable. But when he pulled his robe aside, he only had a speedo under it, and it barely contained his massive manhood.

I guess it's true what they say about black men, although my wife never complained about me. No matter what, this man, Harold, his package was at least twice as long and twice as thick compared to mine.

Then he asked me how I was going to pay for the fifteen hundred dollar dress that my wife no doubtedly would want to keep. Sure, his own wife would probably make it look like a gift, but he, Harold, had paid for both dresses. And if I wasn't going to compensate him, then he would assume that he could fuck my wife, as payment for the dress, just like his own wife did for every dress he gifted her. And he grabbed his crotch, pulling his dick out in one move.

He personally didn't care who he fucked, he said, so if I wanted to take her place, he was fine with that. But, he warned, if my wife would also accept one of the leather dresses, that added another four thousand, at least, to the bill. He expected cash payment, no credit card transaction, and I knew I didn't have that kind of money, we had spent all our savings on this trip to Mexico.

He said a blow job was worth five hundred, a regular fuck a thousand. And if the first blow job was not to his liking, then there was no second chance.

So, the decision was with me. I didn't have the cash, so did I want him to fuck my wife, or would I do the honors? And if I would do it, then the blow job was due immediately, before the women would come up. My wife would never find out, unless I told her.

I had no choice really. I had to protect my wife from him. I knew she wanted the beach dress, and hopefully the leather dresses were never discussed. That meant three blow jobs, because no way could I handle him fucking my backside, and I had to do it right, to make sure he didn't dismiss another bj.

Two minutes later I was on my knees between his legs, pulling his monster completely out of his speedos. My wife has given me a few bj's and I tried to remember what I liked most. And it was not just her tongue making love with my dick, it was her hands around the base, while teasing my scrotum.

I tried to push every thought from my mind that was unrelated to giving the best blow job ever, and as I grabbed his dick, I opened my mouth to take it in.

“It” was huge! Sure, I said that before, but I could hardly breathe anymore through my mouth, and when it filled my mouth completely, more than half was still outside. So I put my hands at work to satisfy that outside piece, but I couldn't even wrap my fingers fully around the dick.

Knowing it was a disaster in the making I started sucking and with my tongue I took the little bit of movement allowed, and tried to lick it along the shaft. But, something I was doing worked, as I heard a moan above me.

The dick was growing in my mouth and I could actually feel the blood pulse through the veins. My mouth stretched to accommodate the extra girth, and I kept the pressure on. “Don't pull away when I cum”, I heard his voice warning me. And it was nothing too soon as the first squirt hit the back of my throat.

I couldn't have pulled away even, as his hand was now on the back of my head. I was drowning in his cum and the only way to survive was swallow all his gunk as quickly as it squirted into my throat. I couldn't believe how much there was, I would have to cum at least five times to match this.

Eventually it stopped and I could breathe again, more or less. His dick was deflating, just a bit, and he was pulling out, as I let him go, while my lips caught his last cum and cleaned him.

I survived my first blow job! Can't say I particularly liked it, but it wasn't as bad as I thought it would be. And in a weird way I felt proud that I got him off. I guess I could do this a few more times to pay off my debt.

But, he started to explain, it was not enough. Yes, he liked my technique, and it did make him cum, but my looks were a turn-off for him. It would be easier to take my rear, so he didn't have to see my face.

Oh god! No, I had to do something. And I only saw one solution. I begged him to give me another chance. I would wear a wig and maybe some makeup. A dress if he wanted me to. I got his interest now.

What about nails, he asked. He liked fingers with long bright red nails wrapped around his dick. And he wanted to see lipstick marks on it. And he wanted me to have a ponytail that he could pull on, without some wig coming off. How committed was I?

It was a two-edged sword. If I committed to his wishes, my wife would certainly find out and she would not like it. And she would offer her body to save me, but in the end she would be disgusted with me. No, she couldn't find out.

Harold had a solution though. He offered me a job, right here in Mexico. He could actually use my programming skills, he said, for some of his endeavors. A job I couldn't refuse, he said, but there was an immediate need for me in Mexico City, and the plane was leaving in less than three hours, so I had to leave right away.

He would explain everything to my wife, and she would be their guest for as long as needed. In the meantime, he knew someone who could give me a complete makeover, so that even my wife wouldn't recognize me, while I worked for him as his maid servant, until all my debts were paid off.

This was getting worse and worse… A maid servant, ready to blow him any time he wanted? Giving up my job back home? What would I do once everything was paid off? Going back to being Reggy? And suddenly be back again? How long would that take? Wouldn't my wife get suspicious?

Harold said I worried too much. He would take care of everything, and my wife would never question it. She'd be too happy living a lavish lifestyle for a while. But, if I committed, it would be for a year, or more, if my debt wasn't paid off by then. And if I wanted I could still be in his employ afterwards as he could indeed use my skills. But, I had to decide. Right that minute. Before our wives were coming up.

I never make rash decisions, always want to mull over them. I don't like to be pressured into anything, and rather say no, than be forced into something. But there was no time here. This was about me or her taking the hit, and she didn't deserve that. She'd be better off if I'd disappear for a while. No forced sex, yet living as a queen. And I would be around to see her happy, even though she wouldn't know. So I gave my consent.

Harold would get a contract drawn up, but he wanted me to give a physical commitment. Another blow job, I figured, but then he pulled something from a drawer and showed me a little cage. A chastity device he said. I was to lock my dick up, until all debt was paid off. I was to be a girl, so I wouldn't need my dick anyway. Right?

I was beyond the point of caring by now. With my future being so unclear, it was just one more inconvenience. So, I took the thing and dropped my pants. Harold had to show me how it worked, a ring around my scrotum and then feeding my dick, which was limp by now thanks to an ice cube, into the cage that would click into the ring. I turned a tiny key and handed it to Harold. My commitment to becoming his maid servant.

Things went fast after that. One of his men walked me to my room, where I changed into normal clothes. I had to open the safe in the room and he took my passport, as well as Jolene's, my wife's, both in a protective pouch. After that he drove me for about half an hour until we reached a place that looked like a salon. I was to agree with everything they would do to me for my makeover, and he would be back with my contract. I realized I didn't even have my wallet on me, and had to trust he'd come back.

At least the woman who took care of me, Alexandra, was very nice, very welcoming, and very understanding. I wasn't the first man she had turned into a woman, and she promised I wouldn't recognize myself even by the time she was done. I didn't realize it was going to take a week though.

Some of the things she did were very permanent, like the hair removal she started with, first thing. And I would have to come back for that in the months to come. Once smooth and fully naked after my first laser session I had to take what looked like a mud bath. And with my eyes “glued” closed and a plastic tube in my mouth I was submerged completely in the dark goo.

When I came out she didn't free my eyelids, but guided me to a bed, which I soon realized was a tanning station, as I could “see” the bright, and hot light all around me, even with my eyes closed. It was so extreme, I almost passed out, as I could feel sweat pour out of my body. A straw was pushed between my lips and eagerly I drank whatever the liquid was in the cup. I figured it was water but it had a weird after taste.

When the ordeal was finally over I realized my eyesight wasn't going to come back for a while, as I was put in a chair, still fully naked, while they worked on my hair and face. And my nails, both on my hands and feet. I was beyond caring by now, although the pain as they pierced my ears prevented me from dozing off. Likewise, a number of pricks in my lips told me my face would never be the same again. And what had to be a tattoo device on my face confirmed that, as some tears managed to leak from my eyes.

After what seemed like hours Alexandra told me that apparently my wife had picked out a nine thousand dollar leather dress, and Harold had told her to prepare my body for penetration, not just blow jobs. I was too tired to object.

Not being able to see at least didn't give me a chance to anticipate what would come next, or I would have ran away had I seen the examination table I was going to be strapped on. With my legs in stirrups, and my body completely immobile, someone pushed something in my completely exposed anal hole. I knew I tensed up, but I couldn't do anything. I almost had to laugh when I realized they were pumping water inside me, and then it rushed out of me again, and it sounded like they caught it in a bucket. After five sessions apparently I was deemed clean, for whatever came next.

I realized they could kill me here and I wouldn't even notice it, but for some reason I trusted Alexandra. That's when I heard a male voice. Was it Harold, coming over to take my anal virginity?

Somehow it felt more like a doctor, as the activity between my legs increased. For a moment I was afraid he was going to cut off my manhood. So I was glad he was only inserting something inside my hole. It was some device, cool, and it probed inside me until it touched a spot that actually felt good, and he approved of my involuntary moan. A second later that very same spot hurt like hell.

I cried out and it was Alexandra's voice who hushed me, which made me feel a bit better. After a minute or so the pain was reduced to some numbing, and then I heard a soft click and a buzz touched that sweet spot inside me, making me gasp. I couldn't stop the wave of arousal that flooded over me, and my dick started going hard.

Started, I say, because an instant pain in my dick stopped it right away. The cage was still there and any growth was prohibited. I panicked, couldn't they see what this was doing to me? The pleasure point was relentless, impossible to ignore, and so was the pain, but I put all my energy in trying to prevent my hard-on. And the only way was by giving in to that pleasure in my rear, cutting every other sense off. And the moment I reached that point I came.

I'm assuming it was an orgasm except it was more intense than anything I ever experienced before. It spread out like wildfire across my body, which made me buck against the straps holding me. With no way to release that enormous tension I heard myself cry out like a bitch in heat.

Apparently that's what they were waiting for as suddenly the sensation inside me stopped, allowing my body to come down and relax again. But before I could close my mouth something was pushed between my teeth. It was rubbery, like a protective mouthpiece, and five seconds later I understood why, as I heard the male voice say “pain” and my sweet spot suddenly hurt like hell. More than that initial pain I felt before. And I cried out, and I knew if it wasn't for the mouthpiece I might have bitten my tongue off.