My Neighbor Dressed Me Up

(I already posted my story on the crossdressing group, here - EP Link - but I guess it's probably more appropriate for this group.)

One strange year I became very close to a girl who lived across the street from us; she was in the 8th grade, I was in the 5th grade. Her mom and my mom decided that she could "watch me" after school until all the parents got home from work, etc., the usual latch-key kid stuff.

I remember she liked to affect an English accent. She had this absurdly funny way of saying the word "again". It was like a full minute long by the time she finished with it. The first few times we were together, she simply dragged me throughout her house and yard, pointing out anything and everything that was important to her. The whole time, her voice wavered in and out of this odd courtly lilt, like she'd been practicing it for so long but couldn't exactly get it just right now that she finally had somebody to really use it on. It charmed me utterly, and I looked at whatever she wanted me to look at, played whatever board game or Atari cartridge she wanted.

Her name was Bonnie (not really). She looked exactly like a princess-long, soft brown hair; large, round, dark eyes with lashes that she liked to bat at me constantly; a slim, virginal body with tiny breasts and pointy hips; she possessed an easy grace like a ballerina, and she always held her chin very high. It was mostly an act to impress, I know now. But she *was* beautiful, and she knew she could use that to use me. However she wanted.

I'd just begun to really notice girls and how good it felt to ram my hard **** against the pillows at night. It wasn't difficult for Bonnie to lead me down all kinds of paths, but the one that we traveled the most was right into her closet.

She was big-time into getting me to dress up in her clothes. Sitting back on her bed, leaned against the pillows, her long legs crossed at the ankles, Bonnie would direct the whole scene. I would stand dumbly for a while and gaze at her bare feet, her shorts where they billowed out to reveal the edges of her panties, her tanned arms crossed and pensively covering her knobby little breasts. Then she would alternately smirk and pout and order me to ***** down to nothing. Then I'd have to put on her panties, skirts, bras, blouses, sandals.

Everything she wore, I wore. We went through the whole closet over the course of a few months. Her panties were the nicest thing to put on, of course. They were simple cotton, nothing fancy, but they were *hers*. Plus, they had that extra little ***** in the crotch, and they rode up my *** nicely when she made me walk around. She let me wear more than a few pairs home, and for many years I kept that small collection hidden inside a shoebox that was shoved way under my bed.

I like the bras OK, but they seemed so ridiculous. Even though Bonnie had very small breasts, there was still this pocket of nothing in the cup, and the things pooched out on my chest as I'd stand there under her inspection. It was nice to feel the straps around my body, of course, but the sight of such a useless garment on me was a bit of a letdown sometimes. Bonnie eventually solved that problem by stuffing a panty inside each cup for me, and that pretty much immediately improved my opinion.

Skirts felt deliciously naughty to me, the way they swished around my legs, the way the air blew up under them, between my legs, tickling the little hairs on the insides of my thighs. Sometimes Bonnie made me pull on her pantyhose, which slid so soft and cool and tight up my legs. Then the skirts would swish against that hose and keep a cool silky sensation running up and down my lower body. It was easy to love how that felt.

I remember trying to imagine if other boys liked that sort of thing. After all, other boys had to spend time playing with girls, right? Were there classmates of mine who wore girls' panties and bras, who liked pantyhose and embroidered hemlines?

Our feet were quite different, so I couldn't wear Bonnie's shoes. She solved this problem one weekend, when she went to visit relatives out of town, by stealing a pair high heels from her cousin. They were black, strappy, and expensive-looking. I remember Bonnie told me she'd get killed if she got caught.

"But it's worth it, *dah-ling*," she intoned, in her best fake accent.

Eventually, she started putting makeup on me; then she began to get dressed up herself. We had "tea parties" (with her old Barbie set) and "walks in the royal gardens" (the scrubby backyard behind the privacy fence). She was my princess, so happy and carefree and giggly/thrilled that we could do what we were doing. I knew I was her slave and that I loved her with all my heart and that she'd let me marry her someday. Then I could do everything she wanted, forever.

Of course, the payoff for me was that, when she finally got around to dressing herself up, I got to see her naked. Like it was part of what she expected, she'd go all the way down to nothing, turn a few times on her tippy-toes, then dip into her dresser for a fresh pair of panties and some fancy knee-length socks. She grew to like her own nudity with me quite a bit, and sometimes I'd even get to undress while she was laying back naked the whole time herself, only getting herself dressed up after I was finished.

But the greatest part of it all was that she finally decided to let me pleasure her. We didn't know it as such back then. She'd just strike up that accent and order me to "lick this… lick this… yes, *dah-ling*, that's divine…." I would suck and nibble lightly on her little breasts. The nipples, budding like they were, felt so soft and tender in my mouth! Her toes went in my mouth a lot, too, and began for me a casual fetish that I still love to indulge even to this day. (In fact, nowadays if I'm around a pretty woman who is barefoot or in a nice black strappy sandal, I have a serious concentration problem.)

I learned to lick and suck on her ***** until she orgasmed. Without a doubt, I was there when she had her first. The look on her face! She even lost her English accent for a minute, long enough to say, "****! That felt so *good*!" In the nicest little clipped southern drawl I could've ever imagined. She liked just the tip of my index finger to be in her *******, wiggling, while I slurped her ***** like a sloppy dog. Then, as she neared her peak, her hands would push on my head, and I'd know to zero in more and more on her clitoris, making my tongue ride it until she was satisfied.

(And she tasted exactly, perfectly, like a luscious, ripe kiwi. The same tart-sweet flavor. The same juicy, sticky mess. I didn't know that was what her ***** was like at the time, of course; but imagine my surprise a few years later at a wedding reception when I got my first-ever taste of a real kiwi fruit! I was asking Mom to buy them, week in and week out.)

We had a thrilling, delirious time-the princess with her long legs and disdainful gazes and soaking-wet *****, and her faithful lady-in-waiting, with a penis that wasn't old enough to come yet, but it sure did want to! Bonnie had no interest in putting it inside her, though, not even out of curiosity. She said, quite simply, that no boy would ever shoot his baby-making seeds inside her; and that was that. Even if I wasn't old enough to really do it, she wasn't the least interested in letting me try. After all, she was getting off already, what did she care?

Her mom and dad kept to their schedules with amazing consistency; never once did they come home early. So by the time they arrived we were always back in normal clothes, makeup washed away, ***** smell banished by Lysol. But Bonnie kept the English accent. Clearly, it amused her parents.

Then my family moved away at the end of that school year, and naturally I stopped wearing girls' clothing every day after school. (Where else would I get access to them, after all?) I did get out the panties I'd hoarded, though, and I liked to wear those quite a bit. Never having bothered to explain it to me, Bonnie had always taken a permanent marker and drawn her name in cursive on each one, right on the outside of the crotch. I liked to think that my hard **** was ******* her, in a way, when I finally started coming: I'd wrap those panties around my **** and spurt rope after rope of my cream onto her finely scripted name.
imunderher imunderher
36-40, M
1 Response Aug 7, 2010

I just have one question, have you been in contact with her since you moved?