"Of course," she said. "I want you to look as nice as possible."
Resigned to the situation, I sat on the bed and fed my feet into the delicate female footwear. They fitted perfectly.
"How did you know my size?" I asked.
"When you came over the other night, I checked your shoe size while you were 'recovering'. Looks like I got it just about right. Looks like I guessed the dress size too. I took a bit of a punt on that, but it seems to fit just about right. Actually, that was quite funny, buying the dress. I knew roughly what size you would be, but the problem was going to be the shoulder width, because guys have got much broader shoulders. I was trying to gauge the size by trying dresses on myself, trying sizes that were really loose on me around the top, and the pesky shop assistant kept trying to give me smaller ones that fitted me better. In the end it became so frustrating that I actually came clean and told her what it was for – for a man. You should have seen the look on her face! I told her it was a fantasy of mine to have my man dress up like a woman, and that's what the dress was for. And you know what? By the look on her face, I don't think she was disgusted by the idea. Quite the contrary, in fact."
As if that wasn't humiliating enough, it seemed she had some other items still in the bag. She pulled out a wig!
"So I'm expected to wear that as well?" I said.
"Yes. I want you to look like a woman, not some drag queen. It's lucky that you've got quite slight features for a man, and you're not at all hairy. I mean, don't get me wrong, you're very sexy as a man, but I think you're going to look hot as a woman too."
Now she was rummaging though the bag for more things. Clearly this whole deal, bizarre as it was, excited her tremendously.
The wig was auburn in color, shoulder length, with a slight curl at the ends. Not unlike her own hairstyle. I slipped it over my head. I looked and felt ridiculous.
"OK, two more items and then we're done," she said. In her hand she was brandishing a black bra and pair of fake breast cups, made of some kind of rubbery plastic. She came around behind me and unzipped the dress, so that it fell down over my shoulders and arms. She slid the bra around my chest and fastened the back, and then inserted the fake boobs. She held my boobs in both hands jiggling them around to settle them inside the bra, squealing 'nice tits!" as she fondled them. Then she zipped me up. Under the dress I was conscious of the bra and how unusual it felt; the thin straps over my shoulders, the elastic of the strap against the skin of my back.
"For the final touch," she said, "lipstick!"
I was beyond the point of arguing now. What does it matter if she wants me to wear lipstick – she's already got me in a dress and heels, a bra and fake tits. She came in close, studying my face intently as she started applying the lipstick. I pouted my lips to make it easier for her.
"All done!" she cried, grabbing my hand and hauling me over to the mirror. I almost stumbled, unaccustomed to wearing high-heeled shoes.
She stood beside me, hands around my shoulders as we looked at the image in the mirror of me as a woman.
"Oh wow, you look so sexy!" she said. "I can't believe it!"
Nor could I. I almost couldn't recognize myself. The dress was mid thigh length, and framed between the hem of the dress and my pumps, somehow my legs didn't look masculine at all. It didn't look like me. Kate was right, I am quite slightly built for a man, but I never would have expected I could so easily be transformed into a woman! Well, it wasn't something I had ever even contemplated before. Clearly my torso didn't show the shapely curves of a woman, but there were my tits, sticking out proudly, and remarkably firm. And they were bigger than Kate's. The dress was cut high at the top, so there was no 'cleavage', but in all respect my tits looked very real under the dress. Even the wig seemed to work; it was obvious a high-quality job, and it sat over my short-cropped hair just right. It was remarkable, bizarre; I looked like a woman!
"Mmmm," she cooed, "I think you would turn heads – male heads – walking down the street like this. You look like an attractive young woman. The only thing that gives you away is this," she said, her hand finding its way to my crotch: "Mmm, your cock appears to have become hard and it's showing through the dress. David, that's not very ladylike!"
Then she got up and scurried from the bedroom, yelling back to me: "Wait there!"
I sat there, turning red in the face. It was true, I had to face the fact: this bizarre little dress up game had given me a hard on. I was wearing a little black dress and heels, fake tits and wig, and underneath my cock was hard. I couldn't deny it, this was exciting me in a weird, kinky kind of way. I felt ashamed. She must think I'm gay! And that thought, the shame I felt, only heightened my arousal as I felt a rush of blood surge into my member and more precum leak out of the tip.
"OK," I heard her say from the living room, "you can come out now."
I stood up and walked into the living room. It was hard to walk in the heels, but I didn't stumble. My heels made a click clack sound on the polished wood flooring in the hallway. Kate was standing in the middle of the living room as I entered the room. She was scrutinizing me. She had shed her clothes, and was wearing nothing but the big transparent cock strapped to her waist. She came over to me, her cock sticking out in front of her, as if leading the way. She came up and embraced me, kissing me hard on the lips, grinding her cock into my abdomen, grabbing my ass and squeezing it tightly with her fingers. I kissed her back. She knew how to kiss.
She stepped back. She looked me up and down, rubbing her hand over my dress, around my ass, feeling me up. Then she reached up and grabbed my tits through my dress, squeezing them.
"Mmmmm," she purred, looking me in the eye. She was panting heavily; her chest was heaving. Her eyes had that glazed, lustful look. Clearly, she was wetting herself under that strap on. "Nice tits," she said.
"Now," she then ordered, "down on your knees. Suck my cock, girl!"
I obeyed. I slid to my knees and took her cock in my hands. She thrust her pelvis forward slightly so that the tip of her cock brushed against my lips. I knew what to do. I opened my mouth and let it slide inside.
"Mmmm," she purred, "good."
I began to suck gently on the head, swirling my tongue around it and gently bobbing up and down on the top of the shaft, only taking an inch or so of it inside my mouth. I looked down my body. The fake tits under my dress were occasionally grazing against her legs as I worked up and down on her cock. When my head bobbed down the hair on my wig would get in the way, so that I sometimes had to brush it aside.
"Harder, suck it harder, bitch!" she cried.
I sucked her harder. It didn't feel so unfamiliar this time. On the contrary, the memory of the first time was vivid in my mind. The tapered tip, the veins, the soft extremity but hard core of the shaft – maybe good wasn't how it felt, but it did somehow feel natural. Well, I thought to myself, this actually is a casting of a real cock, so in essence it's a natural thing. But natural for me to be sucking it? Natural for me to be wearing a dress, impersonating a slut – impersonating Kate? – and sucking a dildo?
I didn't have time to mull over these disturbing contradictions when I felt her cock jam against the back of my throat as she thrust it hard into my mouth. I almost gagged, but she pulled back a bit just in time.
"Girl, you need to learn how to deep throat your man," she said.
Part of me wanted to stop this right now. It was humiliating beyond belief, and that part of me was still wondering how in the hell I had got myself into such an unbelievably embarrassing situation. Then I thought about the photos I would take with my cum splattered across her pretty face. That would be my reward for this ordeal. But then another part of me wanted to please her. She wants me to suck her cock, wants me to deep throat her. I wanted to giver her pleasure. I had gone this far; there was nothing to gain by backing out now. I wanted to take her all the way, as far as she wanted to take this. I opened my mouth wide and plunged my mouth down over her cock as hard and as far as I could manage. But it was still only half way inside my mouth.
"Oh," she squealed, "now you're getting it, slut. Now, just hold it there, just so. Relax your mouth, get used to the feeling of it. Good, that's it. Oh, you look so hot with a big cock in your mouth! Such a little slut!" she hissed as she began to rock back and forth, gently pushing more of her cock into my mouth.
"Does it feel good?" she asked. "Hmm?"
I nodded.
"Good. Ohh, I knew you'd get to like this. Oh David, I wish my cock was real! God, you don't know how great it feels to have a man cum in your mouth! To feel through your tongue his cock pumping out the cum, ooh, the power of it; it's such a turn on! Ooohh, yes, you don't know what you're missing!"
