Just Look at Me Now Ch. 02

When I arrived at my first scheduled play date with the kinky lesbians Jude and Becky, I was extremely well prepared logistically. I had triple-checked the items I'd been instructed to bring and completed all my assigned tasks, including shaving my legs. Emotionally and psychologically, however, I was shakier. I had loved the impromptu feminization we had indulged in three weeks before, but I had never experienced anything remotely like the four hours of service and training we had arranged for today. Nothing to do, though, but to trust my new friends and hope for the best.

I'm always punctual, and on this Saturday morning I was compulsively precise, ringing the buzzer to #201 the moment my phone showed 9:00. Announcing myself as "Nick" on the intercom—I'd chosen "Nick/Nicole" as pseudonyms—I was quickly buzzed up to the apartment, where the memories of our first meeting flooded my mind; this was, after all, the place I'd been dressed up in lingerie to put on a masturbation show for the women's amusement.

Both Jude and Becky were wearing casual clothes, as if this were any weekend morning—no stiletto heels, no leather. After a few minutes of pleasant greetings, however, Jude took control, instructing me to take off all my clothes and hand each item to Becky. I did so with trembling hands and a blossoming erection, and when I was naked Becky took my clothes out to their small balcony and hung them on the railing. Nice touch.

I knew that in their erotic play Jude was typically dominant and Becky submissive; they switched roles on rare occasions, but it would be more than a year before I witnessed that. By now I had abandoned my half-conscious assumption that dominance would go along with size and strength; logically I knew that wasn't true, but at some level I felt it should be, that Becky with her greater height and strength "should" be the top. Now I was obliged to obey both women despite my more muscular frame. A sub-sub, or maybe "sub squared."

Speaking of size, Jude and Becky now sized me up, taking a close look at me as I posed for them hands on head, hands behind back, and hands on ankles. Then they literally sized me up: the first activity of the day was to measure my naked body every which way. Jude had the tailor's cloth tape measure, Becky took notes, and I was told not to speak.

Jude explained that they might someday want to buy me something to wear—could be a mini-skirt, could be a collar, could be my Halloween outfit—so it was smart to get my measurements in advance. She certainly did a thorough job. Working from head to toe and skipping my genitals (we all knew that couldn't last), she measured my head, my neck, the width of my shoulders, the length of my back from neck to waist, my biceps, my sleeve length, my wrists, my chest at its broadest expanse and at bra-strap level, and my waist. She tested my love handles (very small) and chided Becky for being a bit thicker in the waist. We learned that my nipples are exactly ten inches apart. Below the belt she measured my hips as well as my inseam from ankle to naked balls. Then she asked Becky to trade places with her and finish the measurements.

I'd been waiting for my cock to be measured, and standing there silently worrying about it. As a boy I'd been small and scrawny—smallest in my class until a growth spurt in high school. With a small body, or at least with my small body, came a small dick, and I was deeply self-conscious and anxious about this when entering puberty. As an adult, I'd quit worrying so much, and I recognized the stupidity of judging manhood or sexual attractiveness by phallic size. But when a woman approached with tape measure in hand, the old nervous circuits fired anew.

The genital measurements turned out to be more complex than I had anticipated. Becky began not with my penis, but with my balls, first measuring their maximum combined circumference, then making an educated guess at the dimensions of each individual testicle. This of course required substantial hands-on manipulation. Next she used a small cord to find out how tightly my scrotum could be tied, looping the cord around my ball sac and below my penis. Think of putting a couple of golf balls in a pouch and seeing how tight you can make the drawstring at the top. Apparently a 5-inch cord or ring could fit me snugly but safely. Becky emphasized that this would be useful information when we progressed to two things I'd never even heard of at the time—cock/ball bondage and wearing a cock cage. For non-mathematicians, that 5-inch circumference means a ring that's only about 1.5 inches across.

At last it was time for my cock, which of course remained fully erect. Becky took a few quick measurements before announcing "I have a bit of a problem here. If I measure the side of the shaft that's facing me, like this, I get a length of 5 inches. But if I measure the back of the shaft, along Nicole's abdomen, it's only 4.5. Becky was inclined to give me a break by using the more generous assessment; Jude insisted that cock length is always taken along the abdominal side, so my official length was then and is forever 4.5. The engorged girth of my penis was 3.75 inches both at the base and just below the head. I can be precise about all this because part of my homework for the subsequent visit was to type up their handwritten notes.

"So, Becky," said Jude, "Where do you think this penis falls on the bell curve of cock size?"

"Well, it's been a while since I've seen actual dicks up close, but I have to say this one strikes me as below average. It's definitely smaller than our smallest dildo. So I'd say a bit below average in length, and definitely below average in girth."

"I agree," Jude said. "Not a pencil but far from a stallion. Nick, you may now speak. Do you agree with our conclusions?"

"If you think it looks small now, you should see it after a dip in the ocean!" (I make jokes when I'm nervous.) "Actually I must admit you're right—I'm a little undersized. I hope you're not disappointed. I thought I didn't care much about size, but having you measure me made me feel super vulnerable."

"Oh Nick, we're just giving you a little mindfuck," said Jude. "You'll probably never meet two women who care less about big dicks. And besides, even though your junk isn't big, it's nice otherwise—your balls are symmetrical, your cock is straight, and we know from our previous meeting that it works just fine. Plus you like feeling vulnerable or you wouldn't be here—it's a powerful erotic urge that's going to bring all of us a lot of pleasure! We sit in bed at night sharing ideas of what to do with our little pet."

"Right now I'm imagining that cold-water dip in the ocean, whether we measure your shriveled up cock or not," added Becky. "Can you picture a bikini beach party?"

"Oh god, absolutely," gushed Jude. "Matching polka dot bikinis for just us two would be lame, but a video of the three of us could go viral! And we've already got the sound track, that itsy-bitsy teeny-weeny song. No bikinis today, alas, but it is time to get you dressed up as Nicole. Let's see what you've brought; you can spread things out on the couch."

I grabbed my gym bag and laid out its contents: Becky's panties from our first meeting, which I'd washed; my new pink bra and panties; 3 pairs of spare panties ("just in case"), black thigh-high stockings; my 40DD silicon breast forms; pink/black shoes with a 1-inch heel; rose lipstick. "Looks good," Jude said. "Proceed."

I'd practiced dressing at home, so things went smoothly. The hardest thing was managing the rather bulky tags on the panties and bra—I'd been instructed to leave them on until the lingerie had passed Jude and Becky's inspection. After I'd done a couple of twirls to show off my outfit, it got four thumbs up and the tags could come off. Although they were attached only by those thin plastic bands that always fall on the floor and disappear, Jude snipped them off using large EMT shears. A few pair of these were strategically located throughout the apartment for safety's sake—bondage had been known to happen in every room, and in an emergency there might not be time to untie an elaborate series of knots.

"Wait here just a sec," said Jude. She went to the balcony, retrieved my underpants from the railing, and quickly cut them into about a dozen little pieces, which fell to the floor at her feet. "If you're a good girl," she said, brandishing the shears, "I won't have to use these on your jeans." She began to kick at the remnants of my underpants, plus the tags and nearly invisible bits of plastic, to spread them out around the room; Becky joined in. When things were well scattered, Becky told me to clean up the mess and put my dismembered undies in the trash. Bending over with my heavy breast forms felt strange, and I was glad I was wearing a bra substantial enough to keep "my boobs" from popping out.

My next small assignment was to use the half bath in the hallway to put on my lipstick. I'd practiced this as well and did a reasonably good job despite hands shaking slightly with excitement. Becky touched things up a bit when I came out, giving me a little more arch in the middle of my upper lip.

"Now as you know," Jude said, "we've been keeping some lingerie for you to wash. We'd like you to use the kitchen sink so we can watch without us all being jammed into a bathroom. Unfortunately the sink is full of dinner and breakfast dishes, so you'll have to get that cleaned up first. We'll be here at the table so we can chat as you work."

And chat we did. We had learned very little about one another when we'd first met—too preoccupied with the erotic improvisation. Today I was able to share some intentionally vague information about myself (single, mid-level manager at a tech company, born in Boise but a California resident for fifteen years). Becky and Jude had no fear of me telling anyone I was their crossdressing sissy, so I got fuller bios from them. Jude was clearly a brainiac—art history degree from Brown, MBA from UCLA, fluent in Italian. Her career path was complex but had led to a spot in the creative department of a San Francisco ad agency.

Becky had grown up in nearby San Mateo and earned a degree in architecture at Cal Poly SLO, and was now working her way up in San Francisco's municipal planning office. Also no dummy, clearly. They'd met at a munch at San Francisco's Wicked Grounds coffee shop, where you can buy cuffs along with your coffee, or have your grilled cheese sandwich served in a doggie bowl. (How had I missed all this more or less in my own backyard?) The skyrocketing cost of SF housing had driven the women to Burlingame, where they could afford more space and still have an easy train commute to their jobs.

When I'd finished the dishes (with all this cleaning I was already wanting/dreading a future maid's outfit), Becky dumped a pillowcase full of lingerie on the kitchen counter. It was a formidable pile. The white panties I'd been wearing when I got publicly pantsed three weeks earlier were mixed in with more than a dozen pairs of panties. The smaller ones, obviously Jude's, were mostly boy shorts. Becky's larger panties included a few fancy pairs and a few everyday Maidenform briefs in various colors. There were also a couple of thongs, so skimpy and stretchy that I wasn't entirely sure whose they were.

In addition to the panties were one pair of black nylons, not unlike the ones I was wearing, and six bras—clearly three from each of them, easily distinguished by cup size. Becky's were all underwire, like mine; Jude had contributed one sports bra and two beautiful bras, both from Italy.

My instructions were simple: Woolite, cold water, rinse thoroughly, no wringing. I would hang things to dry when I was done. They again sat and watched for a while, as we discussed our tastes in music (I was more conversant with classical genres and they overemphasized pop, but we shared devotion to jazz, musicals, and classic rock). When they were satisfied that I was doing a good job, they left me in the kitchen and asked me to call them when I'd finished. Moments later I heard Sondheim's "Company" in the background.

After all the stimulation of their presence, it was interesting to be alone with my thoughts for a few minutes. It was humiliating, exciting, intimate, suspenseful. I'd didn't want to be a permanent houseboy, or housegirl, but hand-washing our delicates was somehow deeply satisfying. It may be that because Becky and Jude accepted my panty fetish I was able to accept it more myself. I like washing panties—not entirely sure why, but there you have it. I like wearing panties, shopping for panties, and having a drawer full of colorful panties. I like to say the word "panties." I even like typing it. Panties, panties, panties!

"All done," I called when ready. I had arranged all the panties to the right of the sink, everything else on the left, and also made sure items were dry enough that water wouldn't drip on the floor.

"Come on out," they called. I walked to the living room, managing my heels pretty well, and beheld a sight to behold: both women had changed into distinctly non-casual attire.

Becky could have stepped out of a vintage lingerie catalog. Her bra, panties, and gartered girdle, all matching, were a delicate aqua green with beige accents. Her beige stockings, though new, were manufactured of exquisite denier nylon using 1950s-era technology. She wore very high black heels and lavish makeup. Beautiful and curvaceous.

Jude was all in black, much of it leather: a leather bralette above silken black panties, black fingerless gloves, knee-high black boots, and an amulet around her neck on a black cord. Beautiful and intimidating.

"We are ready for your spanking, which Becky will begin once you have hung the lingerie in the hall bathroom" Jude said. "Would you perhaps like to pee as long as you're in there? It's been quite a while since you left home." When I said yes she told me the rules: door open, sitting to pee, panties at ankles. That seemed easy enough, and I really did have to pee, but when I sat down with my cock firm and my panties down and the lingerie hanging all around me to dry and the women walking toward and away from the door to tease me, it took me a while to get a stream going. They didn't actually watch me pee—not this time.

When I came back to the living room, Becky was seated on the middle of the couch. She summoned me with a single silent finger. We had agreed three weeks ago that spanking would be fun for all of us, so this wasn't a surprise. Still, it was hard to wrap my head around the fact that it was actually going to happen. I'd gotten a playful little spanking from a girlfriend decades before—21 whacks on my 21st birthday, but otherwise only my mother had ever reddened my tush. As I assumed my position lying across Becky's lap, I was so excited that I was afraid that any friction on my cock might make me orgasm. Fortunately I found a position where my erection could just rest quietly.

Becky told me not to speak and went to work. She had been spanked many, many times by Jude and put that experience to good use. She began very gently, eventually using many techniques that some of you lucky readers will know—not just whacks, but pokes, squeezes, jiggles, and tickles; rhythmic spanks and syncopated spanks; soft and firm spanks, sometimes two-handed; spanks through my panties and with them pulled down out of the way. After several minutes she had me count down the final ten spanks, saying "Thank you, Becky" after each whack.

They had me go check the color of my ass in the bathroom. Pink but not red. Then it was Jude's turn.

Once I was positioned across her lap she pulled my panties off my butt and gave me one rather hard whack. After a pause she delivered two lighter blows. Another pause, then quick spanks of butt cheeks right, left, right, left. "Let me know when you see a pattern," she said as she began burst of eight rapid spanks.

"You keep doubling it!" I said, just in time to avoid sixteen.

"Well done," said Jude. "Let's play again. I'll just take these gloves off to get a little more sting into it." Then came three spanks, a pause, nine spanks, a pause...

"Powers of 3," I guessed. "Three, three squared, then three cubed."

"Aren't you the clever one! I remember Becky got twenty-seven and damn near got eighty-one. Let's see what else you've got. Here we go..."

A long pause, a spank, then one more, then a pair, then a trio, then five more... I knew eight spanks were next, but what the hell was this famous series called? "Fibonucci! I said. You add the preceding two numbers to get the next one."

"Fibonacci," Jude corrected. "So close, but you still get the eight spanks." These were then delivered with particular spunk—spunky spanks. "You're getting pretty red back here, Nicole, but I think you can handle one more challenge."

Three whacks, then one, four more, another, five more, then nine, then two, then six. Sure, you know the answer by now, but then again your ass is not on fire. Finally the solution came to me as I absorbed 5 more spanks. "The digits of pi?" Yes! Finally those dull math classes had paid off. Just for fun Jude had memorized the first twenty digits of pi, far short of the astonishing record of 100,000+ memorized digits, but more than sufficient for a robust spanking.

This concluded my spanking, except for the mirror check, which showed quite a red ass. Yet no cuts, no bruises, and as it turned out no lasting marks—just rosy butt cheeks for an hour or so. Jude and Becky were clearly quite skilled.

We still had more than half an hour to play—enough time for Jude and Becky to craft an unforgettable orgasm for me. This began with the first bondage experience of my life, though I'd been fantasizing about bondage since adolescence.

It doesn't take a dungeon to play with bondage. My gentle introduction required only a chair and two very large scarves. I fetched the simple chair from the kitchen, placed it in the center of the living room, and sat with hands on knees as directed. With Jude taking my right wrist and Becky my left, they went to work with the synchronized precision of waiters at a Michelin star restaurant. Each doubled her scarf, looped it around a wrist and tied it off—just tight enough that I couldn't pull out. Then they used the long tails of the scarves to bind my wrists to my legs and finally my legs to the chair. I was going nowhere.

After taking a moment to admire their work, they explained that I would be allowed to masturbate before I went home, but would have to wait while they tried to get me desperately eager to orgasm. I felt pretty desperate already after a three hours of stimulation but kept this thought to myself.

"While we have your attention," Becky said, "we need to go over your homework for your next visit. First, we want you in panties 24/7 with exceptions for the gym or doctor's office. Second, whenever you pee, do it just like you did here today— sitting, and with your panties at your ankles. You'll need to seek out all-gender bathrooms when away from home, and if that's inconvenient, all the better! Do you understand, and do you promise?"

"Yes, I understand and I promise."

"Finally" Jude said, "we want you to do some shopping here in town today. Stay right where you are for a moment." Very funny. She disappeared into the hallway and came back with a small reusable bag. "When you leave today, you will stow your gym bag in your car, then use this bag for your assigned shopping." The shopping bag came from a popular boutique on the main drag that sells women's clothing and jewelry. Just big enough to hold a small loaf of bread laid flat, it had a simple design—white background, the store's name (Angelica's) in pink, and three stylized yellow daisies on each side.