As I have alluded to already, Alex wasn’t a completely good boy for me during the time I was sick, and this gave me an excuse to try something I’ve been meaning to do for a while now. It’s all this writing about forced feminization! I guess lots of the things we’ve done might count as that, considering all the ways I have him “help” me – from getting dressed for dates to, umm, “entertaining” them. I do love to get him to help me pick out my clothes (especially the lingerie) we both know will be used to seduce other men. Before I got sick, I’d even taken to having him help me with hair-care (shaving), and having him give me manis and pedis before the dates, too.
But I’ve thought it might be nice having him accompany me a little more often on dates or pickups. Of course, if people thought he was a guy it might cause hesitation with guys not into that, so I’ve been playing with the thought: what if he went with me as a girlfriend? Would that be fun?
He’s never been into cross-dressing. Sure, I have often made him wear panties or stockings when I went on dates – or when I brought them home – but that was mostly to make the other guys feel more comfortable, you know? Or to remind Alex what was happening after I’d left. Last night I thought we might try something a little more fundamental.
“Come here, Alex,” I said.
We Reach an Agreement
He came over, and I gestured in a way he understood. He pulled his pants down to show me his cage.
I gestured a little further, and everything came off. He’s well-trained by now, even if he isn’t above taking advantage of a situation from time to time. When he was standing in front of me with nothing on but the cage, I went to my lingerie drawer and pulled out a g-string and handed it to him. He put it on without complaint.
Next came the bra which I ordered a month or two ago. It’s big enough to fit around him and has nice inserts, too. I put that on him, and he began to look at me with a question in his eye. As is usually the case, I wanted to see how far he would let me go before actually resisting. It amazes me how far he does, and on went the bra without complaint. Next came the blouse and skirt and more alarmed looks, but he obediently stepped into the skirt even though he was somewhat reluctant.
Feminization is Easy!
This stuff is easy! I created a whole elaborate set-up to get Peter to do this in It’s a Woman’s World, and here was Alex just quietly going along with everything I did without a struggle at all! Of course, we’ve had our struggles in the past, so he knows that resistance is futile.
He did resist a little bit when he saw me get out my cosmetics. Or he kind of pulled back, anyway, so I began talking to him. “You took advantage of my illness in several ways, didn’t you, Alex?” I asked as I pulled him closer and began applying the foundation to his face. I think that was the moment of truth right then. If he’d pulled back again and said he didn’t want it before I got the foundation on him it would probably have ended right there – but that’s the way it always is, isn’t it, guys? You can’t decide you don’t want it in time to resist, so we just get our way.
He stammered a little bit about whether he’d done anything wrong while I was sick as I put the foundation on him, and then he began to argue that the little things he’d done didn’t justify serious punishment. It isn’t like I’d gotten out the riding crop! So we argued as I put the makeup on him. I let him say whatever he wanted to say as I tweezed his brows and put the mascara on him, then shushed him as I put on the lipstick. He was ready by the time we’d finished the argument! I wouldn’t say he was exactly ravishing, but he’d do for where we were going, and with the wig on he looked very feminine. No one would recognize him or mistake him for a man in the light we’d be in. That was the important thing.
It was a nice night at the club, and I think Alex made several new friends who will be looking for him next time we go!