Just Look at Me Now Ch. 03

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn.

Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shopped frequently for items I'd been assigned to buy as my homework—mascara, a ladies' razor, a pair of clip-on earrings, nail polish, and so on. I met Becky and Jude every two or three weeks in their apartment, where my spankings grew more intense and my bondage positions more ambitious. I spent a good deal of time spread-eagled on their bed, and just enough time in a hog-tie to appreciate the difference between helplessness and utter helplessness.

Their teasing, both physical and verbal, similarly grew more robust. My cock was routinely referred to as my clit, and I was a "pet," "a kitten," a "sissy," and a "slut." Cock-teasings lasted longer and sometimes featured a blindfold, and when I was allowed to orgasm, I could only do so by using their classic Magic Wand vibrator. Occasionally, no matter how long I'd been aroused or how obedient I had been, I was sent packing with no relief.

Amidst this slow crescendo, two succeeding days stood out. First, we signed me up for a package deal offered by a remarkable salon devoted to transgender and crossdressing clients—not in San Francisco, as you might expect, but in a bedroom community just north of San Jose. I'd learned about it when researching where I might safely shop in person for a wig, a "must-have" item that Becky, Jude, and I all wanted. The salon offered not only wigs and breast forms, but also makeup lessons and products, and even chaperoned excursions for crossdressers and transgender folk.

We made a two-hour appointment for Saturday afternoon of Labor Day weekend for a make-up lesson and wig selection; the package included keeping the wig, whatever make-up we used, and false eyelashes and nails. That morning I drove to Becky and Jude's apartment, where I spent a couple of hours in panties and bra doing dishes, making their bed, vacuuming, and, for the first time, scrubbing their toilets. A maid's outfit was definitely on my Christmas list.

When I'd finished my chores I was allowed to change back into my boy clothes (still wearing panties, of course) for a light lunch al fresco at one of Burlingame's many sidewalk cafes. Then we set out for the salon, about forty minutes away, in Jude and Becky's bright red Prius. The salon was located in an ordinary strip mall with a coffee shop, real estate office, Mexican restaurant, and a few other small businesses. I was relieved to see the blinds down in the salon's front windows, so I would not be on display to any passersby. Yvonne, the salon owner and stylist, proved herself highly sensitive to privacy issues—her clients included closeted crossdressers as well as openly transgender people at various stages of transitioning. I had prepaid with PayPal to maintain my anonymity, so was simply "Nicole" during my visit.

The salon's interior was divided into three areas separated by large open archways. The front room contained a small desk for office work and two display cases packed with cosmetic products, boxed wigs in many styles and colors, gaffs, and breast forms. Displayed on one wall were a dozen bra/panty sets and one gorgeous nightgown.

The second room, much larger, was where the real action would happen. It was equipped with two professional salon chairs, good mirrors and lights, and zillions of brushes, lipsticks, foundations, color charts, and so on. This was truly a liminal space, a specific area fully dedicated to gender transformation.

After we introduced ourselves to Yvonne and reviewed our expectations, I was ushered to the third area, which featured two small changing booths, a lunch table, a fridge, and oversized lockers for regular clients who kept their women's clothing here. Becky and Jude invited Yvonne to watch me change into the outfit I had brought along, but she wanted to keep her eye on the front of the shop. Thus only my friends watched as I stripped down to my panties and then put on a bra with breast forms, stockings and heels, a simple navy blue skirt, and a floral blouse (hyacinths, mainly). My boy clothes went into a vacant locker.

I fervently believe that anyone should be able to wear whatever they like without the gender police interfering. I salute the muscular guy with a bushy beard who has the courage to wear a gown or miniskirt. When I visited the salon, however, I was curious to learn whether I might "pass" as a woman. Might I someday walk down the street in a dress and not be noticed? Could my face look feminine, or perhaps even pretty? These desires felt primarily expressive, not erotic. (Don't worry—sexual escapades are galloping our way!) I wanted to get some of that gender fluidity that everyone was talking about for myself... not for sexual gratification but to connect with a growing sense of my whole, authentic, complicatedly gendered self.

My salon session was thus devoted to making me look like a woman one might routinely encounter at a coffee shop or grocery store, and thanks to Yvonne's skill and experience I think we got there, or at least very close. The session consisted of Yvonne applying makeup to the right side of my face and letting me mimic her work on my left. She explained beard masking, color selection, foundations, setting powders, and so on—all the things you can find on transgender Youtube tutorials. Becky and Jude took a few notes and helped me correct little mistakes.

I still cherish the photos we took on my smartphone. Were you to glance at these quickly you would most likely "read" me as female. I didn't look beautiful, perhaps not even pretty... but I at least reached "not unattractive"—quite acceptable for a first attempt.

I learned two things from this. First, the wig was utterly transformative. Of the dozens of gender markers we all carry (clothing, voice, body shape, posture, gait, etc.), the hair sends one of the strongest messages. When you add makeup, false eye lashes, and long, colorful fingernails, the gestalt tilts strongly toward the feminine. Of course I recognized my male self looking out from under those long lashes, but I also looked very much like my favorite niece, just older.

The second thing I learned is that I craved photos. In my first discussions with Judy and Becky I had stipulated no photos or video, and they had not pressed me on this. Now I wanted a visual record of my feminization, and we quickly set ground rules to make this work—my phone or camera only, and my control of editing/sharing. I now have a huge trove of photos and a chronological record of my journey; Becky and Jude have dozens of the best pics with my face hidden somehow (another great use of a wig). I love knowing that they can share these with their friends whenever they like, and they've had a blast showing people what it's like to have a sissy serve you martinis while wearing a tutu.

I had the option of undoing all the transformative work before heading back to Burlingame, but Yvonne, Jude, and Becky all urged me to spend some time en femme, and I agreed. I was slightly aroused, slightly nervous, but mostly very happy to feel a new way of being in the world. It helped that two months before I'd been escorted down a crowded street wearing only panties. Today could hardly prove more embarrassing than that, even if someone noticed I was crossdressed.

After a short walk across a moderately crowded parking lot I was granted the rare honor of riding shotgun, and off we went. The key thing that happened was that nothing happened. At first I couldn't help feeling that every person in every car was driving along wondering if they would see a crossdresser today. Of course in reality they were in their own little bubbles with their own little worries, paying me no never-mind.

"This is too easy for you," said Becky from the back seat as we drove north on I-280. "I dare you to go on a short walk with us, say from one end of the Stanford Shopping Center to the other and back." Whoa, baby! I had long indulged in Truth or Dare fantasies of feminization, though my real-life ToD experience was limited to adolescent play that went no further than brief displays of girls' breasts and guys' dicks. Now I faced a real-life Dare, and the Truth was I wanted it. Feeling giddy, I accepted.

We exited the freeway at Sand Hill Road, zipped past the venture capitalist offices, parked at the shopping center, and walked from Nordstrom's to, ironically, LaBelle Salon and Day Spa. This was apparently my day for lessons, for the walk taught me a few things. Above all, I liked it. I liked to imagine that someday I might spend a full day dressed up and out in public, or shop for women's clothing while dressed in women's clothes. My deep voice was a barrier to genuinely "passing," but I could perhaps manage pretty well if I kept my mouth shut, if only because many people are extraordinarily unobservant.

With my companions by my side, my nervousness faded and I began to feel safe as long as we kept moving. People were looking at their phones, or the shop windows, or the cute dogs, or the truly pretty women, and I walked along as if invisible. I didn't speak, and I didn't dare enter a store or sit at an outdoor bench. On the move and out in the open, however, my exhilaration matched my self-consciousness, and I was almost sorry when we got back to the car.

In stark contrast, I experienced a nervous moment when we got back to Burlingame. Jude and Becky's reserved parking spot was in the underground garage of their building. No one was there when we parked, and no one came out of the elevator when we got on. As soon as the elevator doors closed, however, I felt trapped. We only had to go past the ground floor to the second floor, but there was no way to know who we might encounter on that short trip. I punched "2" and prayed we would go straight there, but the elevator lurched to a stop at "G" and a young couple got on and punched "4," the top floor. They were dressed in tennis clothes and apologized for being all sweaty. Jude said something like "No worries" and I stood petrified, staring appropriately at the red panic button. The bumpy ride in the old elevator lasted less than ten seconds, but that's an eternity when your fake boobs are gently jiggling the hyacinths on your blouse a mere six inches from some guy's elbow.

"How are you, darling?" Becky asked me when we were safely inside the apartment. "That must have been interesting!"

"I was scared," I admitted, "much more than in the salon or even walking through the shopping center. I was just stuck there, and they were so close!"

"I'm pretty sure you batted .500," Jude said, "very impressive for an elevator ride. Hats off to Yvonne! I think the guy had no idea, but the woman—what's her name?—was at the very least suspicious. Do you agree, Beck?"

"Absolutely. Pretty sure she knew, but not him. She's 'Sandy'—absurd name for a woman with black hair. I wonder if she'll make the connection when she crosses paths with Nick in his guy clothes. Sandy's boyfriend was too busy ogling my boobs to check out Nicole's." (My "boobs" were as big as Becky's, but she was showing a lot of cleavage whereas I was a model of modesty.)

"Stella! Stella!" Jude fake-yelled in her best Stanley Kowalski imitation. This meant it was time for a Stella Artois. "Nicole, please serve us on the balcony. Bottles are fine, no glasses needed. If you're willing to sit outside you may bring one for yourself."

Their balcony, spitting distance from a busy street and sidewalk, was an oddly private space: drivers and pedestrians seldom looked up, and the building residents on this side almost never used their balconies, likely due to traffic noise. So we shared a beer in the cool shade on that warm day and talked about my adventures, their upcoming trip to Napa, and Becky's anticipated promotion at work.

"There's something else I'd to talk about, Nicole." A slight shift in the timbre of Jude's voice signaled that she her dominant side was emerging. "I'd been thinking we'd give you a spanking now or have you perform a strip tease and a wanking show before sending you home, but I have a new plan to propose. It depends on your being able to spend tonight and much of tomorrow here, however. Is that possible?"

"Yes, I can do that," I replied. There are some advantages to living alone.

"OK, good. You've talked a lot today about how nice it feels to try on a feminine self—not just as a fetish but as something deeper. I suggest that we allow you to remain in that mindset through the evening and night, but that we fast-forward your feminization and servitude tomorrow morning. Still interested?"

"Yes, absolutely, but can you please explain what you mean?"

"I can give you some hints, at least," Becky said. "We've been talking about how to push your boundaries, and I'm pretty sure I know what Jude is talking about." They exchanged glances and nods to confirm their agreement.

"For the purposes of sex play, anatomical males have two main orifices," continued Becky, "although with enough ingenuity the smaller openings can be put to use as well. Tomorrow morning Jude will teach you how to use your mouth for her pleasure, and I will begin training your anus. Essentially we will be colonizing two of the most sensitive and intimate parts of your body. Rest assured our play will be completely safe, though at times, well, let's call it uncomfortable."

"And to be clear," added Jude, "while today was very much about you—our spending the day letting you express yourself in new ways—tomorrow will be all about us, our whims, our pleasure, our power. And definitely no orgasm for you, though it would be delicious to hear you beg for it. You know the phrase "consenting adults"—we'll be the adults and you'll do the consenting! So, shall we proceed, or do you want to clean up now and go home?"

I hesitated. Truly hesitated. I had no time constraints all weekend, but I'd already had so many new experiences that I was afraid of psychic/emotional overload. And I was apprehensive about just what would be required of my mouth and ass. Still, every time I had taken a risk since meeting these women, I'd been richly rewarded. After a pause I took a deep breath and said, "I trust you both, and I appreciate everything you did for me today. I will do my best to please you."

I spent the rest of the evening behaving, to the extent possible, as if I were just one of the girls. We made a salad and cooked pasta together, with pesto they'd made from the two potted basil plants on their balcony. We finished off a day-old bottle of Chardonnay as we cooked, and enjoyed a robust Nebbiolo with dinner. How strange and fun it was to see stains from my very own lipstick on my wine glasses (one for white, one for red—very classy!) After some dark chocolate and decaf espressos, they helped me open the "divano di letto" (sofa bed) and gave me the day's closing instructions: remove my makeup and sleep in my panties. They said goodnight, collected my boy clothes, and locked themselves in the mistress suite.

Surprisingly I did manage to get some sleep that night between long stretches of aroused and nervous anticipation. I was wide awake when they first stirred Sunday morning.

Despite their very casual appearance when they joined me—both wore pajamas and slippers—my service and obedience began right away. As soon as we had said good morning Jude told me not to speak again until granted permission. Instead I would listen and obey.

Following their instructions, I put on my bra with breast forms and my 1-inch heels. I made coffee for them, prepared them a hearty breakfast (scrambled eggs, orange juice, and sourdough toast), and cleaned up the dishes. I stripped the sheets from the sofa bed and refolded it. When I brewed a second carafe of coffee I was allowed a cup along with a bowl of Raisin Bran. I stood silently as they finished their coffees and their Sunday morning routines—Becky reading the paper and Jude tackling the Sunday NYT crossword. In ink.

Once every square was filled—thank heavens Jude is an expert cruciverbalist—Becky left the kitchen for a minute and came back with a pair of red high heels, a pair of knee-high black boots, a rag, and a spray bottle of shoe cleaner. I cleaned everything thoroughly as they watched. When the footwear had passed inspection (by size I could see the boots were Becky's, the heels Jude's), Jude set a kitchen timer and told me to meet them in the living room in 30 minutes. That would give me time to use the bathroom, shave my face, test my newly acquired makeup skills, and don my wig. I was to wear the bra, panties, and low heels I already had on.

By my current standards, with all the practice I've had since then, that first solo makeup effort was about a "C." I was rather proud of my efforts at the time, however; I struggled a bit with the eye shadow, and things were not as evenly shaded as they'd been at the salon, but my appearance was definitely transformed, especially with the wig. And of course I finished on time—I was not going to blow things this early in the adventure.

Becky had been busy too. Precisely as my timer went off she entered the living room carefully made up, dressed in elegant lingerie, and wearing the boots I had just cleaned for her. She inspected my makeup job, adjusted my wig slightly, whacked my ass a couple of times, and gave my balls one good squeeze. "You'll want your bra nice and tight for this morning's activities," she said. "Hold onto your boobs while I shorten the straps." Standing in front of me she made a small adjustment to each strap. Then she walked behind me and changed the band from the loosest to the tightest clasps. "Now kneel down," she commanded when this was done, "and look straight ahead."

When I was on my knees she moved away from me. With the carpeted floor I could scarcely hear her steps, but after a few moments I heard a drawer open, then close. I had time for two deep breaths before I felt the collar being placed gently around my neck, under my "hair," and then adjusted to a snug fit. "Perfect!" said Becky. "I'm so glad we measured you last month! Hold still and don't touch it."

I hadn't been expecting a collar that morning—it didn't seem to have much to do with my mouth or my ass—but once I had been collared I should have expected the next couple of things. You can likely guess, but I was surprised—first at the unmistakable click of the lock, and next at the sound and feel of the leash being attached.

"Don't tell Jude I forgot to check the padlock," she said. "I was so focused on being quiet that I totally forgot." I was pretty sure this was a bit of gaslighting. Say 95% sure. "So, the essential rule you must follow when leashed—the only rule, really—is to follow your handler just as a well-trained dog would: on my left side, just off my hip, attentive to my every movement, changing pace and direction smoothly so that the leash never tugs. Nod if you understand." I did.

"When you can walk confidently in stiletto heels, you'll be allowed to stand while collared. But for your first lesson we start with the basics. Best if I remove your heels." She slid them off and set them to the side. "Now onto all fours," she commanded, shoving me between my shoulder blades. When I was in position she stood to my right and said, "Nicole, heel!" And off we went.

Never before had I so appreciated the splendor of bipedalism! Crawling is hard, awkward, tough on the knees, cramp-inducing. And then there's the wee embarrassment of being led on a leash. When was the last time I had crawled, aside from brief moments in the crawl space under my house? Maybe playing war games as a ten-year-old?