Panty Raid, Panty Trade

If you're a closeted crossdresser like me, surely you have felt the fear of being caught, humiliated, scorned, or even physically assaulted. Such worries arise in my waking thoughts and are a recurring theme in my dream life: I've long had dreams in which someone glimpsed my panties, or stumbled across my stash of bras. The premise of such dreams is occasionally plausible—my fly is unzipped, allowing a glimpse of panties—but more often the premise is wildly unlikely. I may wear panties to my dermatology exam, for example, or have a massage with the impressions of my bra still clearly visible on my skin.

I feel anxious in such dreams, but they are also highly erotic, and they provide interesting scenarios for sexual fantasies and masturbation. This story, however, is about the one time in twenty years of secret crossdressing that I actually did get caught. I learned a couple of things that are perhaps worth sharing. First, rare events do happen, so you need unrelenting vigilance to keep your secret. Second, being found out might not be disastrous.

I got busted during one of the few trips in my life where I've packed no boxers, only panties. This happened three years ago, on a trip from Silicon Valley to a tech conference in Montana. At the time, I was working as an electrical engineer for a start-up company that specializes in programmable logic devices. The conference was half scholarly gathering and half corporate boondoggle, or perhaps 80% boondoggle given the resort setting outside of Whitefish, near Glacier National Park. People did deliver papers and give presentations, but the schedule was light, and there were plenty of opportunities for hiking, mountain biking, horseback riding, fly fishing, and more.

Like most attendees, I arrived Wednesday afternoon in time for the cash bar and opening banquet. My presentation—ostensibly a discussion of chip architecture, but really a thinly disguised plug for a forthcoming product—was Saturday morning, one of the last few meetings. A few folks flew home as early as Saturday afternoon, but I had booked my suite through Sunday night to have one full day of unimpeded sightseeing.

Most of the conference-goers worked in California, and lots of us knew one another. We could have met closer to home in Mountain View, but here we had real mountains and real views. My suite, in fact, had stupendous views; I had registered asap and snagged perhaps the best accommodations on the property. The room matters to the story, so pay attention! My suite, the "Bighorn," was one of two units in the resort's newest building; the first floor of this structure was divided between a modest single room, named "Osprey," and, as part of my suite, a combination office/living room with a Murphy bed and small ADA-compliant bathroom. The entire second story belonged to my suite and featured huge picture windows on three sides, high ceilings, a king bed, an imposing audio/visual setup, and a luxurious bath/shower area. My company was picking up the tab, roughly $600 per night even at the reduced conference rate.

I arrived in time to unpack, set up wifi, check my email, shower and shave, and enjoy a local "Bushwhack" IPA on my balcony before heading to the lodge for the happy hour and banquet. There I caught up with old friends, made a few new acquaintances, and started to plan some extracurricular activities like a guided fly-fishing trip Friday evening.

I also met a young entrepreneur who would hire me two years later at an exorbitant salary, but more importantly for this story I ran into a former colleague named Marisa. She and I had worked together for nearly a year at Intel before taking our chances at different start-ups. I remembered her as whip-smart, focused, and detail-oriented on the job; at social events she was engaging, warm, and witty—great company. Photos on her desk at Intel also showed her sky-diving, river rafting, zip-lining, and spelunking—adventures that seemed incongruous with her practical, button-downed demeanor on the job.

We chatted during happy hour, and though we each had dinner commitments, we met up again for after-dinner drinks in the lodge's great room. After a couple of cognacs Marisa said she was a little worried about finding the way back to her room in the dark, and it was only then that I discovered she was staying in the "Osprey." I was not only confident I could find the right path through the woods, but I'd brought along the small but powerful flashlight that came with the suite for just this reason.

I said goodnight at her door and had just opened my own when I heard her call out. I believe her words were "Shit—my room is flooded!" And indeed her carpet was soaking wet. It was easy to find the source of the problem—a badly leaking water supply line to her toilet (clean water, thank god)—but my shutting off the valve did nothing to remove the many gallons of water that already covered her floor. We called the front desk and, long story short, the only thing they could offer was to get her a room in Whitefish.

Meanwhile I had lots of room, two beds, two baths... so of course I said she should share my suite, and I insisted that she take the upper floor. This hurt, but chivalry dies hard. I grabbed all my things and carried them downstairs, and the resort staff moved Marisa's things, replaced the one towel I'd used, and began damage control in the "Osprey." I should perhaps make clear that there was no sexual vibe about sharing my lodgings—just former colleagues adjusting sensibly to an unfortunate event. Marisa was certainly attractive—long dark hair, blue eyes, delicate features, and a good figure—but we had been coworkers with no romantic relationship.

Getting the luggage and clothes and rooms keys sorted out took only half an hour, and while the flooded room was an unwanted jolt of excitement, I fell asleep quickly and slept soundly.

When I woke up around seven, slightly hung over, I instantly realized that in collecting my things the night before I might not have emptied the drawer where I'd put my dirty clothes—just one shirt, a pair of socks, and the only thing I cared about, one pair of panties. Uh-oh. I threw on jeans and a t-shirt and began frantically checking my drawers to find that these items were indeed missing. Fuck, shit, piss. I would have to retrieve my items the first time Marisa went out, praying she didn't find them first. There were tons of drawers up there, easily triple what she needed, so I had a chance.

At first I had no luck. Marisa had heard me moving around and called out "Good morning" from the top of the stairs. If she was hung over too, it didn't show; she was dressed for the conference and had done her hair and makeup. She begged me, however, though I had "done so much already," to bring back a real coffee from lodge—the coffeemaker in the room was new, but the coffee itself sucked. Good to know people don't change: she had always been a caffeine addict and a coffee snob. Of course I would have preferred that *she* go get a coffee, but I agreed.

My errand took about fifteen minutes, and when I returned and called out jokingly "Honey, I'm home!" Marisa came downstairs She took her coffee and one of the scones I'd brought ("You're a lifesaver!") and said she'd enjoy them out at one of the picnic tables overlooking the lake. My chance! When she stepped out, I counted to ten, peeked out to make sure she was some distance from our unit, and raced upstairs to retrieve my things. I opened the bottom right drawer and found my shirt, my socks, and this note on the resort stationery:

"Something missing? Ha-ha! I seem to be the only suspect in this caper, so I confess—I am your panty thief. The pair you left here is in the closet safe, along with all the clean ones I found downstairs. You were very well supplied for such a short trip!! Now that I've got your panties I'm considering my options. I'll be back soon to tell you my plan."

So I sweated bullets for what seemed like an hour but was probably half that. She was either a very slow eater or she was giving a lot of thought to her plan. Turned out to be the latter: though it took her a little time to formulate the plan, it was a doozy. When she at last returned, she had me sit on the Murphy bed while she walked slowly around the room outlining what was in store.

"As you're well aware," she began, "I know virtually all the women at the conference—we're still outnumbered in tech and tend to stick together. I will select some of my colleagues whom I most trust and tell each one, individually, that I've boosted your panties and want to trade a pair of yours for a pairs of hers. I'll then be putting you in whatever panties I choose through Sunday. To minimize your vulnerability I'll ask the women to commit to a version of the famous Las Vegas slogan: What happens in Whitefish stays in Whitefish."

"Really?" I asked. "Are you serious?"

"Oh yes, I'm absolutely serious—I'm not going to waste this once-in-a-lifetime opportunity. So, assuming some women agree, as I'm confident they will, here's a run-down of who will know what:

I will know quite a lot—whose panties you are wearing at any given moment, and which women at the conference know about your fetish. If they choose to tell me, I may know whether they are just keeping your panties for a souvenir or if and when they may actually wear them.

Each woman will know that you'll be wearing panties nonstop throughout the conference. I won't volunteer that I'm proposing the same panty trade to other women. If asked about that I won't lie, but I won't share any names. They can imagine whatever they like.

You, of course, will be in a pickle. Some women will know your secret, but you won't know who, so you'll undoubtedly suspect everyone. When you give your paper, some may be in the audience; they may be mentally undressing you and visualizing their panties beneath your trousers.

Let's see... what else? Oh, unless you are careless I'll be the only one to actually see the panties on you, but here in our suite I will see them as often as I like, so you can expect to spend considerable time wearing nothing else.

I know this will be fun for me, I imagine it will be fun for my friends, and I suspect it might even be fun for you. If you agree to my plan we're all set. If not, I'll have to consider my options, but given the current situation I don't see how you can get off any easier."

I must admit I did think her plan would be fun, if nerve-wracking, but I was afraid of it spiraling out of control and was looking for a way out. Some of the options that raced through my mind were ridiculous. Abandon the conference and leave Marisa with my panties to show to whomever she liked? Ask the inn to bring the safe's master key only to have them discover that I'd locked up my women's underwear? Call the county sheriff to report misdemeanor theft? My counterproposal was essentially a plea for mercy: "Well, you could simply give me back my panties now that you've teased me, or maybe choose my panties for me but not tell anyone else."

"Yes," she replied, "of course I considered those options, but I much prefer my plan—it's bolder, more complex, more creative, and more fun for my friends and me, and again, maybe even for you. Have you considered that you left your panties in the drawer precisely because some part of you wants to be discovered?" I actually had thought of that, though I put more blame on the cognac.

"Let's proceed, then, shall we?" she asked, or perhaps directed.

"Um, yeah, I guess... I mean yes, OK."

"I assume you're wearing panties right now—the one pair not in my possession?"

"Yes."

She then took a couple of steps away from me, hitched up her knee-length skirt (a pale solid color, let's call it tangerine), pulled down her panties, and stepped out of them. They were, and still are—I'm wearing them as I write this section—ivory colored boy shorts with a lacy fringe. "So, this is our first trade," she said, pointing to my pants with a simple gesture whose meaning was unmistakeable. It was just the lift of her index finger that said "Off with your pants!"

I used my feet to yank my shoes off, removed my belt as a stalling tactic, and took a deep breath. Then I undid my classic button-fly jeans and took them off, tossing them on the bed.

"Very pretty," said Marisa. "Take off your shirt too so I can have a good look. You might as well get used to it."

So I took off my shirt, plus my now-ridiculous socks, knowing that Marisa would see my painted toenails (red) before long anyway. My legs were shaved, of course, but back then I still had pubic and chest hair, and though I shaved my armpits I don't think Marisa ever noticed that. In any case I now stood in front of Marisa wearing just my Maidenform full-coverage panties—a floral print in navy and raspberry. "Turn around," she directed. "Yes, very pretty panties and a nice ass to boot. I can see you've kept up your gym routine. Now let's trade."

I took off my Maidenforms and we exchanged panties. "Me first," she said, putting on my panties while adroitly keeping her privates hidden, just barely, by her skirt.

Now it was my turn to put on her boy shorts. Throughout this entire encounter my cock had been gradually swelling, with intermittent setbacks when fear took over. By the time Marisa was admiring my Maidenforms I had a "firm-on," and now I had a full-blown erection. The boy shorts were only slightly too small—I'm athletic but only 5'4"—but they stretched tightly enough over my genitals to reveal size of balls, length of shaft, and circumcised head pretty clearly.

"I see you really are having fun," Marisa said, pointing to my groin again, but this time noting the little wet spot of precum on my panties. "Well, I want to grab another coffee, maybe even another scone. I've got an unexpectedly busy day ahead of me! See you later." And she was gone.

I'm no expert on the physiology or neurochemistry of sexual arousal, but that was an all-hands-on-deck moment for me, on the level of losing my virginity. I didn't have to pinch myself to prove I was awake—I was fully awake, actually living the kind of experience that I had only dreamed and fantasized about.

I had just enough sense to grab a few tissues before lying down on the Murphy bed to masturbate. I didn't want to make a mess in my new panties, which I might have to wear all day, and I didn't want to leave a mess in the bed for housekeeping (no tip is big enough to cover that). A few minutes later I had a tidy but amazing orgasm, memorable not just for the circumstances but also for its intensity. As I ejaculated I thought that this moment would more than make up for whatever embarrassment I might face in the coming days.

As my nervous system and breathing and logical thinking gradually regained their equilibrium, however, I revisited that judgment with growing skepticism—was a great wank or two really worth the risk?

In particular I began to think very specifically about how many and which of my panties Marisa now possessed. The ample supply she had mentioned included at least six pair of my everyday panties, comfortable and easily hidden numbers that I could and did wear all day every day back in California. But I had also packed two pair that I would never have dared to wear outside the suite. These were strictly for arousal and masturbation. One pair was fire-engine red, with copious ruffles (not much but ruffles, actually). The other was my most extreme sissy panty, pink satin with white lace trim and giant white bows at the hips that actually held the panties together—tug on the bows and the panties would just fall off. Soon someone out there might know they were mine.

Meanwhile I had a conference to attend, so I took a quick shower, put on "my" boy shorts and the rest of my business casual clothes, and walked over to the lodge and its meeting rooms. I was hyper-aware of Marisa's panties, of course, but for the moment I felt safe; there hadn't been time for her to orchestrate a panty trade, and she had a conference to attend as well—managing my underwear was not her sole occupation.

I attended two sessions that first morning, one quite instructive and the other dull. Marisa wasn't at either, so had either chosen different presentations or spent her time networking. I glimpsed her only between sessions (getting more coffee), and at the outdoor lunch she was seated several tables away, her back to me.

After lunch I returned to our suite to check email and maybe have a quick nap before going for a hike. (The weather was perfect and none of the scheduled presentations looked particularly interesting.) I had handled most of the emails when Marisa unlocked the door and entered.

"Oh good," she said. "I was hoping you'd be here. I want to have a quick chat, but first strip down to your panties—and let's make that your default option unless I tell you otherwise." Housekeeping had closed up the Murphy bed, so I draped my clothes on the desk chair as I undressed, putting shoes and socks underneath.

"Those look sooo cute on you," she said, admiring her panties on my body. "I wish my ass looked like that. I was wondering, did you jerk off after I left?"

I'm a rotten liar and in this case didn't even try. "I'm not surprised," she said, "but you might try abstaining from now on. It's up to you, but the more sexual energy you have pent up the more intense the next few days will be." Good point.

"I also wondered if you went upstairs and looked at my bras, maybe put one on to masturbate?" I had not. "It would be OK," she said. "Do you wear bras at home, and how about dresses, skirts, blouses?"

"I sometimes wear a bra," I admitted, or rather disclosed. With Marisa, at least, this didn't really feel like admitting something wrong. "And I have a very small collection of women's clothing."

"I bet it's fun to play dress up! Good for you... I bet a lot guys fantasize about it but are too scared. At SF Pride I always enjoy seeing bearded guys in dresses. To each his own, right? Anyway, masturbate or don't, but keep in mind I'll be coming in and out with no warning." Duly noted, as was the fact that she attended Pride events. Was she gay? An LGBTQ ally? Or did she just like seeing one of the greatest shows on earth?

"Most importantly," she said, "I want you to know my plan is going swimmingly! I've completed two panty trades, and two more will be done before dinner. So far no one I've asked has said no! That means I can take my panties back now and give you a new pair for the afternoon."

She looked into her purse, saying "decisions, decisions" as she weighed which panties to give me. Then she swiftly reached in, grabbed a pair, and threw them to me. I caught them—told you I was athletic—and realized instantly that there was almost nothing to them. It was a bright yellow thong, big enough around the waist but obviously not designed to accommodate male genitals. (Such panties can be easily found online, however; if you don't know, now you know.)

I took off Marisa's panties, tossed them gently to her, and stepped into the yellow thong. This was not going to be comfortable. There was of course zero coverage for my butt cheeks, something that's always made me feel extra vulnerable, even when wearing thick pants like jeans. But the real problem with thongs is like the ballroom at St. Patrick's Cathedral—there isn't any. Thongs always move my junk around in unpredictable ways, and I have to stifle the urge to put my hand down my pants to adjust things.

Erections are also challenging, and I'd been getting gradually stiffer since Marisa had returned. By the time I put on the thong I had a hard-on. I have a rather hefty cock—not award-winning but more than respectable—so the low-cut thong left about four inches of my penis sticking out above the waist band.