Fiction by Miss Ivy Ohmigosh
I made it. I’d come back to the lingerie shop. I’d been thinking about it for a couple of weeks, telling myself I could go through with it, buy myself panties and a bra. If the cashier asked who they were for, I would say “a girlfriend.” But why would the cashier ask, anyway? What business was it of hers?
It was a small shop on a side street and it looked like it had been there for a long time. It was narrow but was crammed with racks of panties and bras and nighties and shapewear and camisoles and teddies and pantyhose and bodystockings. I had discovered it when taking one of my long lonely walks and ever since then, I’d wanted to go back and start my collection of women’s lingerie. I’d been thinking about this for a long time and I wanted to take action. I’d moved to this Midwestern city, far from my family and boyhood friends on the East Coast, so that I could be alone with my dreams and obsessions and finally give in and dress to my heart’s content. So what was I waiting for?
I had a beautiful bra and panty set in my hand, hanging together on their little hanger, but my heart was pounding so hard I couldn’t get myself to walk the twenty feet or so to the counter. The counter lady was waiting on another customer so I used that as an excuse to stall. The store was empty of clientele except for us two customers; I didn’t have any temporary office work today, so I was able to go on an off-hour. I pre- tended to browse some more, fingering the soft nylon of a bright pink baby doll nightie, and the lace on the low-cut front of a beige chemise. And I kept trying to work up my courage to go to the counter.
Then suddenly I got the insane idea of just walking out with the bra and panty, stuffing them under my jacket. I looked around and the store didn’t seem to have any hi-tech surveillance or even those electronic doohickeys that set off a buzzer when you walk out with unscanned merchandise. Like I said, it was an old store and so I thought maybe, just maybe…
I knew that stealing lingerie wasn’t the answer to my problems, but I was on the verge of tears from the tension and humiliation of imagining the counter lady even smiling at me sideways as she rang up my purchase…
So I moved closer, only a few feet from the door, propelled to thievery by my fear of being exposed for what I wanted—exposed to a counter lady as the crossdresser wannabe I was.
“Where do you think you’re going with that?” A firm red-manicured hand grasped my forearm just as I was about to open the door and exit the store.
I couldn’t even croak out any answer as I looked up into the face of a gorgeous but stern-faced, beautifully dressed blonde woman who was at least four inches taller than I was. But who was she? I had never seen her before.
“I saw you via surveillance in my office,” she snapped, pointing to a small shadowy wooden door that I hadn’t noticed because it was obscured by a rack of long yellow nightgowns. “Don’t be fooled by the old school charm of this store. It’s completely up-to-date, you little felon. And I’m the owner here.” She didn’t let go of my wrist.
“I’m sorry,” I gasped, “I don’t know what got into me!” My voice sounded two octaves higher than usual. “Oh please, ma’am, I’m sorry, can’t we just forget it? I wanted to—to buy these for a girlfriend, but—but—”
“What girlfriend?” the blonde lady laughed. “YOU’RE the girlfriend you have in mind! Come on, honey, admit it—you wanted to take these home to have a date with yourself!”
“No, no, no, ma’am! No, no, no!” But I started to cry. My years of picturing myself as a girl, imagining myself dressing like one, and being treated like one, suddenly exploded in very feminine behavior in front of this total stranger.
“Unbelievable,” said the lady. “There doesn’t seem to be a vestige of male left in you. Look at you blubber, oh dear!”
She still held my wrist. She wore colorful bangles on her own wrist which jangled as I tried to break away from her. But since I couldn’t, I handed over the bra and panty on its little velvet hanger, tears streaming down my face.
“Please don’t call the police,” I whimpered. I looked around and saw the other customer staring at me with goggle eyes and open mouth. The counter lady, however, seemed to take it all in stride, as if she’d seen something like this before. “I don’t want to go to jail!” I wailed to the blonde lady as she tugged me toward the little office.
“You think I can let you get away with this? Impossible!” said the owner. “However, there is a way you can make up for your crime. Quit giving me such a hard time—come with me into my office.” She left me no choice, really—the strong fingers of her hand dragged me behind the rack of nightgowns and into the small room.
Finally letting go of my wrist, she closed and locked the door behind her. It really was a tiny office, with purple walls and light coming from a green shaded lamp over the desk. There was a doorway in the back that led to shadowy stairs. “Wait,” I said, only sniffing now, “I don’t see any surveillance monitors in here.”
“Who said anything about monitors? I ‘surveilled’ you through the peephole in the door, missy!” And with her vibrantly red-manicured forefinger she pointed to just such a hole.
“I’ve caught a number of naughty little crossdressing shoplifters that way,” she said.
“I’m not a crossdresser!”
“You just want to enjoy some pretty lingerie? That doesn’t make you a crossdresser? Oh, oh I forgot, dear me, you were buying this for a ‘girlfriend.’ Well, unfortunately if you don’t do EXACTLY as I say, this bra and panty are going to be entered into evidence at your trial and your ‘girlfriend’ will probably never get to enjoy them—if you’re convicted and sentenced to jail, that is!”
“Here, take this!” I fumbled for some cash in my pocket. “I’ll pay you for them now! Just don’t take me to the cops!”
“Oh, I can understand why you’d be scared of them,” said the blonde lady. “A little pansy like you, so nervous and ready to cry at the drop of a hat, would be lost in jail, even overnight! All those rough tough prisoners, once they got a look at you, would pull down those jeans of yours and fill your prissy ass with a real man’s cock!”
I just stared at the lady, amazed that she could have guessed at one of my dirtiest and most shameful fantasies: of being put in jail and treated like a girl, forced to suck cock and take cock in my behind over and over. And forced to perform striptease shows where I dressed like a showgirl, and then had to do gangbangs with the prisoners, guards, and warden!
“Come on, dear heart,” she said, “there’s no thought in your head that I can’t imagine. I’ve run this lingerie shop for years. You think you’re the first shaky transvestite I’ve seen? Hardly. In fact, I wait for you ‘girls’ to come in here—the shoplifting ones, I mean, the ones I can capture—because I have a very special interest in helping you ‘ladies’ realize your innermost dreams and desires.”
I slowly dropped into a chair near the wall. In a way I was suddenly relieved. I’d always fantasized about running into someone like this, a woman who knew about the type of desires I had, a female who would help me explore them. I’d grown up in a small, conservative town, which hadn’t been affected by all the ideas of sex- ual freedom that you see online or in the media; no parades in support of LGBT rights in my hometown! To the people there, guys who were interested in anything other than the “normal” were considered “homos, queers, and faggots.” That’s why I’d had to get out once I got my degree at the nearby community college, away from everybody and everything I knew, away from my critical parents and my macho friends, to explore my dreams elsewhere. They knew nothing of my inner life and I didn’t dare share it! But even now, fifteen hundred miles away in a strange city, I still carried around the shame inside me, and I called myself names without any help from anybody else. When I fantasized being dressed up like a girl and having sex with a guy—not because I was gay, but because I was really a GIRL!—I got most turned on when I imagined him calling me a “dirty sissy cocksucker” as he crammed my face with his dick. I was afraid I would always carry around the judgmental mind-set and bigoted beliefs of the town I grew up in…and I couldn’t fool myself. I wasn’t a girl, I was a guy, and if I wanted to wear panties and dresses and heels and bras and suck dick, I just HAD to be a “dirty sissy cocksucker”…right? Right?
“My dear, you look so thoughtful,” said the store owner. “Where are your thoughts going? Are you imagining what it’s going to be like with Gail?”
“Gail?” I said.
“Yes, Mrs. Gail Durvette—me. Because I give you this choice: to be dressed as the girl you crave to be, or to be turned over to the police as the shoplifter you already are.”
(Continued in Chapter 2)
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