For the next hour we sat on the edge of the bed while she bombarded me with questions about my sexuality, how long I’d been doing it, why I was doing it, whether I’d been forced or coerced as a child, and if I really expected her to accept such perverted behaviour. During that painful hour, I sat there with my bathrobe wrapped around me, still wearing her white lace French knickers and matching bra underneath.
I squirmed at her questions, answering with short sentences, all the time blushing brightly and wondering when we would leave me alone to change out of her underwear. At nineteen years old, I had been busted for the first time, even though I had quite some experience of borrowing Jane’s undies, and my older sister’s while growing up.
There was something about being dressing up as a girl that stimulated my senses, making me feel sexy, horny and yet somehow complete all at the same time. My slim figure with practically no body hair and my fair complexion made it quite easy for me to pass as a young girl, especially when wearing makeup. I had a collection of photos of me on my computer, in which I swear nobody would have been able to tell if I was a boy or a girl.
“You’re a total pervert!” she said finally, standing up and walking out of the bedroom, “I need to think about this.”
Now that the grilling was over, I became very scared of what would happen next. As I got changed back into my own clothes I thought about the prospect of Jane leaving me. I was terrified. Jane was the most beautiful and intelligent girl I had ever met. I had flashbacks of seeing her for the first time, her long dark hair, her beautiful dark brown eyes and pouty lips. She had a terrific body too, with ample breasts and a slim waist. I remembered watching her walk away from the table that night we were in the restaurant together, seeing her cute round butt swaying beneath that clingy little black dress, and the slenderness of her tanned legs beneath those sheer stockings.
Jane was four years older than me, and much more worldly-wise than me. She was constantly teaching me new things and introducing me to new and interesting people, but she was never a snob. I hoped she would forgive me for my behaviour and that we could continue our lives together.
—
When I walked back into the living room, Jane was sitting there with a magazine in her hands. She looked up at me with an icy stare that sent a shiver down my spine. I turned to walk toward the door, thinking it would probably be best if I left the house for a while.
“Where are you going?” she asked sternly.
“I’m just going to take care of some things in the yard.” I replied.
“No, you’re not!” she said, raising her voice, “You’re not going anywhere until I know what else you’ve been up to!”
I knew that I had no choice. When Jane got upset she was in control. If I had left the room she would have pursued me into the garden, and if I didn’t comply with her demands, she would make it her mission to find a way to make me regret it. I immediately understood the risk, and could picture her on the phone to my mother, telling her how she had caught me in her panties and bra, and how I had been dressing up in my sister’s clothes since I was a boy.
I sat down in the armchair opposite her, my arms folded in resignation, and waited for more questioning. Stupidly I had thought that one hour of Q&A was enough, but she wasn’t about to stop.
“Is it just underwear?” she asked.
“Mostly.”
“What do you mean, mostly?”
“Sometimes I’ve tried on stockings too.”
“And dresses?”
“Yes.”
“Have you worn my dresses?”
“Yes.”
“And makeup?”
“Yes.”
“But why?”
“I don’t know.”
“What do you mean, you don’t know? Is it like a compulsion or something?”
“No, it’s not a compulsion. Well sort of. I just like it.”
“You like dressing up like a girl?”
“Yes.”
“Are you gay?”
“No, I already answered that. I like girls.”
“Do you masturbate when you dress up?”
“Sometimes.”
“Not always?”
“No.”
“Do you masturbate into my panties?”
“No!” I shouted.
“I’ll take that as a yes,” Jane replied solemnly, “Have you ever been out while dressed up?”
“No!” I answered, getting upset. “It’s just something I do at home.”
“This is too weird. You want to dress like a girl in private, you’re not gay, but it turns you on?”
“Yes.” I replied sheepishly.
“I need to do some research.” Jane said after a couple of minute’s silence.
—
Contrary to my initial fear, Jane didn’t leave me. In fact, the incident wasn’t mentioned again for the next couple of weeks, except for Jane telling me she had done some research, and that she had made some “interesting findings about people like you.”
I had contemplated telling her that I would stop the behaviour, but I feared that it wouldn’t be possible. I had been dressing up in girl’s clothes since I was about eleven years old, and the fact that Jane now knew about me had made it all the more tempting to indulge. Only three days after the initial incident, I had rushed into the bedroom as soon as Jane left the house, slipped into my favourite pair of her red stretch-nylon panties and bra and whacked myself off in front of the mirror. The fact that Jane knew somehow made it even more permissible in my mind. After all, at no point had she told me I wasn’t allowed to borrow her clothes.
—
One afternoon shortly thereafter, we went out shopping together.
“What do you think of these?” Jane asked me, holding up a pair of light-blue fullback panties with a little yellow bow on the front. “They’re quite cute, for a silly little girl.”
We were in the lingerie department of a major retail outlet. Initially we’d been looking for some new wallpaper for the study, but Jane had wandered into the ladies’ intimate apparel section and I had dutifully followed, expecting her to have spotted something for herself. Instead, I quickly realized that she was shopping for me. The pair of panties she held up was XL, instead of the usual L that she purchased for herself. I started breathing heavily with excitement, my cock immediately starting to swell inside my pants.
“There’s an adorable matching bra! Look at that little hearts pattern. It’s such a lovely set for a young sissy princess!” Jane said, pointing at the hangers.
“Uh, yes, it’s very nice.” I mumbled, my heart thumping like crazy.
Jane casually picked out a few more panties with equally girlish pastel tones, adorned with pretty patterns and bows, some with lace trims, and each more feminine than the next, all in size XL.
Jane handed the merchandise over to the cashier, a young girl of about eighteen, with a freckled face and a short blonde bob. She was a bit skinny for my liking, but nevertheless looked quite cute in her skin-tight jeans and clingy white t-shirt. She delicately folded the items and put them to one side before asking Jane if she wanted them gift wrapped.
“I would normally, but my little princess has already seen them.” Jane responded, nodding her head toward me.
The girl looked at me with a puzzled face, while I flushed bright red.
Jane leaned in toward the girl and said quietly and factually “He likes wearing girl’s clothes, but only at home.”
The girl sniggered and started to guffaw upon hearing this news. I caught her eyes staring at me in disbelief as a pulled away from the scene. I rushed out of the store and toward the car park.
—
When Jane caught up with me a few minutes later, she stepped into the car and handed the bag over to me, saying “There you go, little Miss Panty Princess. I hope you like them.”
“Why did you tell that girl?” I asked, still shocked at what had happened, “She didn’t need to know!”
Jane looked over at me for a moment, inquisitively. She then reached over to me, put her hand on my crotch and grabbed my stiff cock still throbbing hard from the whole experience.
“Someone doesn’t seem to mind.” She said, winking at me and unbuttoning my fly.
That was my first ever experience of Jane sucking me off in a public car park. She ducked down quickly and slurped my member deep into her throat, swirling her tongue around my shaft while she vacuumed the sticky cum right out from deep inside my balls. The whole episode only lasted a few seconds, from her soft lips gripping firmly around the head of my cock, to her pushing downwards until my shaft was completely engulfed. For a second I thought she was going to swallow my balls at the same time!
The thought of her teasing me about wearing that cute girly underwear and now her pleasuring me in a public place was incredible. I sat there thinking I was in heaven while she drained me, and licked the tip of my cock until she had swallowed every last drop.
“You’ll pay for this!” she said, laughing at me wickedly.
—
Later that night we went to bed early, and I gave her a massage for an hour or so in the candle-lit bedroom with soft music playing in the background, gently rubbing essential oils into her soft skin, taking great care to knead her back until she was totally relaxed. I sat across her thighs while she laid face down, at first running my hands slowly up and down her back, and then sliding my throbbing member between her butt cheeks and deep inside her vagina, holding it there as it swelled up inside her, feeling her buttocks pressing against my groin. I knew it was something she liked very much, and it seemed like an appropriate reward for her having not only bought me some cute girly lingerie of my own, but also having given me that blowjob earlier that afternoon.
Jane groaned as I pulled out gently until the head of my cock almost slipped out of her, and then pushed myself slowly deep inside her once again. I loved the feel of her oily skin rubbing against mine, and the tightness of her pussy as I teased her as deeply as I could. We lay there for several minutes, me lying on top of her with my face buried in her neck, gently biting her soft skin and nibbling her ear as I teased her with my stiff member. I loved the smell of her perfume and the freshness of her cleanly washed hair. She was sublimely feminine, and I wanted her so much.
“Put your panties on, my little princess.” She whispered to me.
While still inside her, I reached over the side of the bed and grabbed the bag of undies that she had given me earlier that day. I quickly located the pair of pastel blue panties she had first shown me, and softly pulled out of her in order to put them on.
While I slipped into the panties, Jane turned over onto her back, watching me as I struggled to tear off the store label.
“Ooh, they’re very cute!” Jane exclaimed, “Let’s see you in that bra too!”
I took the matching bra out of the bag and put it on while Jane took care of removing the store label from the panties. It only took a couple of seconds for me to put on the bra and adjust the straps, as I’d had plenty of experience growing up. I’d often wondered if my sister would notice that the strap lengths had changed, even though I had always been careful to put them back exactly as I had found them.
“What a lovely little training bra! Just perfect for my little panty princess!” Jane, giggled, “Now come and fuck me, you naughty little girl.”
I slid my shaft through the right leg of the panties, pulling them to one side, and proceeded to insert my cock between Jane’s sweet shaven pussy lips. She was dripping wet with excitement, her breasts heaving as I entered her. She grabbed my ass through the cotton panty material and pulled me deep inside her, looking straight at me.”
“What are you?” Jane asked with wild eyes.
“What do you mean?” I started to say.
“You know what I mean. Don’t play games with me.”
“I’m a panty pervert.”
“You’re a silly little girl who thinks she’s a princess. Now, tell me what you are.”
“I’m a silly little girl who thinks she’s a princess.” I said shyly.
“You are indeed. Now fuck me and I’ll teach you to be a real princess.”
With that, Jane held even more tightly onto my ass and used me like a giant dildo. We humped like that for a couple of minutes until she came to an orgasm, swiftly followed by me coming inside her. I was exhausted by the day’s events, and I quickly fell asleep.
—-
When I woke up about an hour later, Jane was lying beside me, wide awake.
“What are you?” she asked softly.
“I’m a little girl who thinks she’s a princess.” I replied, laughing.
“A silly little girl,” Jane said sternly, “You need a new name, and some lessons. Don’t think it will be easy.”
A strange feeling came over me as I realized that Jane was serious about her intentions. I was about to argue that it was just a game and that it didn’t need to be taken so seriously.
“If you want to leave now, you can by all means. But, if you want to stay with me then you’ll need to learn how to be a real princess, on my terms,” Jane said, “And I have a feeling that a girl like you wants to learn.”
“Yes, I do” I acquiesced.
—
