Right now, I feel like fantasizing. But maybe that's counterproductive. I just love that thought that I'm willingly doing something not only naughty, but damaging to my masculinity. That's what I love: I'm being offered a chance to destroy my manhood, and I take it, because I cannot resist the pleasure of being feminine. I love the confrontational aspect of it: I am in complete control of the situation, and I choose the dark side because I love it so much.
What would I do now in such a situation? Let's say that one of my fantasies comes true, and I am captured by women who are taking over the world. I stand naked in front of them. I have seen them dress other men up in women's clothes, if only to mock the conventional gender roles, to question why it is that only women wear frilly silky lacy underwear. They would have me there in front of them, and present me with a choice: wear this lingerie, or we'll make you wear it. How would I react? Would I pretend that it's repugnant to me? Would I feign indifference, and hope to heaven that I could wear it? Would I try to act hesitant as I slip into it clumsily and nervously? Or would I eagerly accept their invitation and prance around effeminately to our mutual delight? Would I admit to having worn it of my own will before, once I'm dressed up? Or would I vehemently deny it, and try to conceal my pleasure? How about like this:
A beam of sunlight, harshly bright, shook me out of my deep slumber. I had absolutely no idea where on earth I was. I was completely disoriented. My surroundings were totally unfamiliar. Have you ever awakened with that distressing feeling, only to realize a second later that you have been sleeping so deeply, in a somewhat unfamiliar place? Well, I actually was in an unfamiliar place. The walls were bright red, the carpet plush, and there was plenty of bedroom furniture other than the bed I lay in.
I shook myself awake, trying to piece together the events that led me into this unknown location. But I couldn't move my arms: each arm was shackled to the bed. My clothes felt strange. It felt as though there was a strap on my chest, but I didn't think it was connected to the bed. My underwear felt light but tight. I had enough movement in my arms to be able to lift the bedsheets. To my astonishment, I found myself wearing women's underwear.
I must have lain in bed for hours before anything happened. I wanted desperately to escape, but I didn't want to alert anyone. I figured that if I called for help, I would simply be restrained by my captor(s). Why the Hell was I wearing women's underwear, and why was I chained to the bed?
What had I done the night before? I couldn't remember for the life of me. But somehow, I ended up here, dressed like a girl, and trapped in a stranger's bed.
[Here's where the story can diverge according to how experienced I am]
I tried hard to piece it together. Someone evidently knew about my little secret now. I must have gotten extremely drunk or stoned somehow, and gotten involved with someone, and shared my most secret, most embarrassing fantasy. I had never intended for anyone to ever find out that I wear women's clothes. Obviously, someone knows now: someone other than me must have chained me into this bed. But whom? And what for? Nonetheless, my shame and desire to escape far exceeded my curiosity. I could not abide by anyone knowing about this. Unfortunately, I was stuck, and could not escape, as much as I tried.
The noise of my struggling must have awakened my captor. The door opened, and in stepped a voluptuous young woman of immeasurable beauty. "Ah, so you're awake at last!" she bubbled.
"Who are you? Where am I? What am I doing here?"
"Don't you remember, sweetie? Have you already forgotten our little tryst? You told me that you'd remember my name in the morning. You haven't lied to me, have you?"
I was speechless.
"Well in that case, I'll try to jog your memory." She jumped into the bed and started playing with my bra and panty straps. She was teasing me. "Don't you remember how you got into these? I thought it would be something that you'd never forget."
She started rubbing my dick through the silk panties. Just as I had always fantasized. I came all over her hand, feeling so incredibly feminine. Then it started coming back to me.
I was in her bedroom. Not this room, but in a different room. We were making out. She was down to her panties, and I was buck naked. I was playing with her undies, because I just love women's underwear. That's when she caught me totally off guard.
"You like my underwear, do you?"
"I sure do!"
"The way you're touching me, it's almost as if you like them more than me."
"Well," I said, trying to be witty, but probably blushing, "they are pretty sexy."
"How would you like to wear them," she purred, somewhat shyly.
"What?"
"Trust me! I'll make sure that you'll enjoy it."
"You're serious."
"I sure am!"
I hesitated a bit, unsure of what to say. I never really thought about wearing women's underwear in front of a girl before. But I knew how much fun it could be. I just wasn't sure if it would be wise to let on that I was into that kind of thing. I take my transvestism very privately. "Why do you want me to wear your underwear?"
"Just trust me! You'll love it!"
"What makes you think I'll love it?"
"Well, you're thinking about it, aren't you? That tells me that you're probably not repulsed by the idea."
I'm sure I must have blushed. "Yeah, so?" was all I could say.
"Will you do it?" she cajoled, rubbing against me. "I'll make sure that you won't regret it." She whispered that in my ear erotically.
"Okay," I said, "if that's what turns you on."
With that she giggled and led me to her dresser. In it was a huge variety of ladies' undergarments. "Pick out anything you like out of there. Anything!" She must have sensed my giddiness. I shook like a leaf. Here I was doing with another person what I did only in the utmost secrecy. I looked at her undies, and picked a nice frilly panty and bra set. I would have picked it out for myself anyway, I think. I was about to put it on, as I have so many times with similar garments, when she offered to strap me in. She must have supposed that I didn't know what I was doing. I felt so girlish when she snapped my bra. No one had ever done that to me before. I was feeling very sexy.
By now we were both in her undies. She had me prance around for her. I was nervous, I was clumsy. She giggled.
She fucked me with a two-headed dildo. Right up the ass. She was on top, taking me like a girl, my legs spread wide to accept her. I swear that the whole time I felt like I was a girl, with her caressing my effeminate bra strap, and teasing my hair. Something in the way she handled me made me feel that way.
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