I had already given my approval for Brittany to invite Jacob and Deshaun over to fuck her while I watched and helped. It didn't help my cause that I was already wearing panties with CUCKOLD emblazoned across the front and back. I had gotten used to them. Initially they were a gift from Jennifer. Now they felt normal, a fact that did not go unnoticed by my hot wife. She moved so seamlessly between asking to invite the black studs over to adding what amounted to a complete feminization package as a condition. It was not really a condition, she just told me that it was what was going to happen. It seemed an untenable task to express reluctance, much less refusal. I didn't answer her at the time. I supposed that she took it as my tacit approval. Or maybe she wasn't worried about my approval.
The alternative was that she would go back over to Eric and Jennifer's and I would be left alone at home like the first time. It seemed an honor to be allowed to take Jennifer's place and also be in our own home. Plus, I figured that if they hosted Brittany again that Eric might be there also. Brittany was definitely following Jennifer's lead as far as becoming black owned. We had always had a satisfying sex life since we were married. At least I thought so. Now with Brittany having been fucked so many times and so deeply, making love to me was a real letdown. However, she did love it when I got her off orally. I also fucked her and came inside her. I don't know whether she really loved the coitus or maybe it was a way to get me to satisfy her orally while I sucked my cum from her pussy.
A few nights later, after I had finished eating my cum from her and satisfying her orally, I decided to ask about the feminization aspect.
"Honey, did you really mean all that about me dressing up when your black boyfriends come over? You were just kidding, right?"
"Actually, Al, no, I was serious. I mean I am serious. That isn't going to be a problem, is it?"
"It is just that, well, Honey, I don't want you and Jennifer, much less Eric think that I am gay."
"Who said anything about being gay, Al?"
"Well, just think of it. I would be eating another man's cum from you while dressed as a woman."
"Again, what does that have to do with being gay? You said that you would do anything to make me happy. I really get turned on by seeing you and even thinking about you wearing your pretty panties. You seem to be okay with that. You have already cleaned another man's cum from my pussy as has Jennifer. She only wore panties when we had the party at her house. But you have to admit that Jennifer is a 'playmate' type, so she is the epitome of feminine. You just need a little work and I want you to experience this with me. Don't you want to be there?"
So, there it was. Either man up (or in this case, 'girl' up) or Jennifer would get to service my wife's sloppy pussy. I was caught. Well, not exactly as bad as I made out. I hoped that my initial reluctance would provide some plausible deniability for being feminized. Brittany thought it was just a continuation of my role as cuckold and also allowed me to be there for the whole thing. Being that she had already been with these men, she didn't need me for safety. She had freely given her married white pussy to three black men so far.
"No, it is okay, Honey," I said, "I just don't want you to lose respect for me. That's all."
"Oh, Honey, Baby," she said, "You have been so accommodating so far. I love how secure you feel in our relationship that you want me to experience such wild sex. I want you to feel a part of this. In no way do I want to humiliate you. It is just that the panties are so sexy. I know you don't mind those because I threw out all your old men's underwear and you haven't noticed. And you are a very beautiful man. I have thought about this. Your face has a gentleness about it. I think when we remove all your body hair real smooth, get a close shave on your face and apply the proper cosmetics that you will look lovely. Hell, I am afraid what might happen is the guys would want to fuck you instead of me. I am just kidding, Al. Will you do this for me? Just this once? Unless you really like it, then we can do it together. I am the one who should be wondering if I am gay. I so enjoyed Jennifer making love to me with her pussy. And, well, yes, I ate her out also. Let's just think of it all as an extension of our new awareness sexually. Okay?"
"Well, when you put it that way, Honey, I would be happy to become your 'lesbian' lover." I said.
Fear and excitement both filled my head. Would this change my persona? Would I still be able to function as an alpha male in my business? This had to be a very hidden dark secret. I took some comfort in the fact that Jennifer and Eric possibly stood more to lose if any of our relationship became public. Eric's friends knew how important it was to be discreet. It was time to grant Brittany's wish and service her fully.
When Brittany announced the date for her studs to come over and service her, I again was filled with fear and trepidation. The guys knew that I was her husband. I had no chance of convincing them that I was a woman. Regardless of how Brittany praised my pretty face, I would still be a man in lingerie. She told me that we were going to make some trial runs that week. She had purchased the specialty makeup for crossdressers and transgendered women. Her normal makeup was not quite right for me. With the special base and a close shave, she assured me that my face would indeed look feminine. I kept all my body hair under control and we were going to make sure it was all neat before the big event.
That week, Brittany made up my face every night. She was looking for just the right combination of highlights and tones to make me look as feminine as possible. She would not reveal my clothing for the meeting until we were almost ready to receive our guests. She had purchased realistic breast forms and high heels that fit and were going to match my outfit. She did try out some different styles of clothing but assured me that it was just for an idea of fit and sexiness. I was actually stunned when she made me up that first night and made me keep my eyes closed before she fixed the new wig on my head. She was right. My face did lend itself to feminine transformation. She already had said that my legs were better than half of the women she knew.
Everything was normal at our house until about ten o'clock Saturday morning. Brittany had me go to our bath where she painted my toenails and applied acrylic fingernails. My hands are not large and the long nails seemed very effective in making them look even smaller. With no body hair, my natural complexion was good enough to look in character. I was going to wear some form of hosiery and something to cover part of my body. The parts that were going to show, Brittany assured me would look soft and feminine.
"Heck, Honey. You might even pass. The guys are going to be tearing up my married pussy all night and might not pay too much attention to my 'girlfriend'.
I showered and got all the supplies for the bar stocked. I made little sandwiches and placed them in the fridge. I knew it would be a long night. I was sure that the guys and Brittany would need some nourishment to keep up the activity. I was wearing a mid-calf robe of Brittany's. My little dick was held by a tight gaff that she had purchased along with the breastforms. I was in seamed stockings and garter belt along with a tight bustier and waist cincher. Brittany had also ordered a small tutu type skirt to hide any male semblance if my little dick did not cooperate. My white stilettos set off the seamed stockings and I felt like a really hot chick.