I picked him up at the beach. I love the sun, the lake, the boys. I wanted to experiment. I remember how awkward it was for me in high school, when everybody struggled with their newly discovered sexuality. I, myself, was unsure of myself, and therefore vulnerable. The boys I knew then, I now realized, must have gone through the same feelings of uncertainty. I wanted to test a hypothesis.
It was far more difficult than I thought. Tyler was completely intimidated by me. He had been staring at me in my string bikini all day long. I was a goddess to him. He had no idea how to handle my approaching him. Normally, I would have simply basked in the attention of all the gawky teenage boys, but I needed my test subject. He was perfect, the typical male 18 year-old: skinny, pale, falsely confident, fairly good-looking, easily seduced. His friends (especially Sarah, his little girlfriend) were incredulous when I approached him with a blunt proposition: to ditch them and come with me for a good time. He stammered like an idiot, his insecurity exposed, before he accepted. When he did, I kissed him full on the lips, and pretended to fawn all over him.
I gave him the rules in my car on the way home: I would entertain him all summer for free, as long as he would break contact with everyone he knew, and stay at my place. I allowed him to call his parents to tell them he'd be at a friend's house for the rest of the summer. They protested, but could do nothing about it. It was only hours later that the horny little bugger thought of clothes. I told him I'd take care of that.
The first night, I let him explore my body to his heart's delight. I first commanded him to feel me all over, as much as he wanted, but without removing my bikini. I didn't let him touch his erection. I wanted him to get hornier than he'd ever been in his life. I'm quite confident that I succeeded. That made the coup de grace easy.
I stripped out of my bikini, and ordered him to pick it up, and put it on. I made it quite clear to him that he could only go further with me if he complied. He had an awful lot of trouble with the bra, so I helped him get it on. I snapped his panties playfully after I hooked it on. He was livid with humiliation, so I deliberately grazed his cock as I stepped away to get a better look at him.
As expected, his gawky skinniness and youth made him look fairly androgynous in my bikini. If not for the slight hairiness, the shallow chest, and the huge erection, he could have passed as a scrawny 13-year-old girl with a butch haircut. He was just about my size, if not a little smaller. He would make a fine student.
I caressed him and fondled his nipples, and told him how adorable he looked. He ejaculated almost the instant I touched the front of his panties. I asked him if he felt sexy when he wore my bikini. He was even unsure of this, but he did agree. I worked him up again, still in my bikini. I had him do a little dance for me, and encouraged him to do it as femininely as possible. Boy, did he ever respond! He was slinking around like Britney Spears!
After allowing him a few more orgasms, I got him ready for bed. I had him slip into one of my nighties. He was still unprepared for this. Nonetheless, he tentatively caressed his silk-clad body, exploring this strange new garment against him, and looked incredibly feminine as he did so.
He quickly made a connection between wearing my clothes, and "feeling sexy," as he described it. I allowed him to think that he could continue being a boy, but at the same time allowed him to experience his feminine side as often as possible. I got him to start taking hormones because it would increase his sexiness.
I took pictures of him in my nightgown, and threatened to show all his friends, to post it at his school. That scared him into obeying my every command.
The second day, after I had him all shaved and pulling on a pair of panties, he asked me, "This isn't going to turn me into a girl or anything, is it?" I remember his exact words because they were so innocent, so trusting. I rubbed my body up against his, and assured him, "Yes, Tyler, it will turn you into a girl. The more you like it, the more girlish you become. And I can tell how much you love it! You'll be a girl in no time!"
The boy practically panicked. He struggled to escape my caresses, and to tear off his panties, but I persisted enough for him to give in. There's no telling what went through his mind as he came. When he came for the third time, still wearing my panties, he cried. But he never took them off.
After only a few days, I didn't even have to encourage him. He was already starting to act more like a girl, taking on female mannerisms, and even asking me, sheepishly, to wear certain items of clothing. He couldn't contain himself when he wore my clothes. It seemed to make him even hornier now when I reminded him how his enjoyment is directly proportional to the rate at which he would become female. I would swear he would act more femininely then, too.
After a month, the hormones were already starting to have an effect. His nipples were growing, and his body hair wasn't growing back. He was blossoming into a woman before my eyes.