Unwrapping Orlo

I was relaxing in my room on a Tuesday when I got a very suspicious text from my roommate:

"orlo you really trust me right?"

"yeah of course whats up?"

"ok I want you to get in the shower and when you get out sit on your bed in something cute and slutty. I've been thinking about what you said the other night"

"uhhhhhhhh the fuck? you don't even like me like that?"... "and what happened to that guy you were talking to"

"nonono its not for me"... "trust me if you were telling the truth i think you're really going to like this. so do you own a bra and panties or what?"

"jesus christ"... I really paused to consider whether I wanted to admit to owning a pair of girly underthings. Most roommates don't talk about shit like this, right? But I decided she already knew enough about my perversions that there wasn't that much risk. "mhhh i might"

"sly bitch of course you do"... "okay take your shower now and put just those on then text me"

"okay IM TRUSTING YOU. you fucking better not make me regret that"

*****

Natalie and I (Orlo -- it's German or some shit) share a room in a flat near a small college in NYC. And yeah, before you ask, money really is that tight. We are always bumping shoulders but I was NOT going back to the dorms after the experience my first year. And anyway, Nat and I get along well enough. Hell, she's probably my best friend here, as you would be able to tell by our conversation the other night. I'll take you through it:

We had both had half a bottle of the cheapest wine we could get at the corner store. There wasn't anything happening and we're both introverted anyway so we decided to get tipsy and do what had become surprisingly comfortable over the past year: say stupid shit for hours on end until one of us passes out.

We're both in STEM, so typically Natalie would bemoan endlessly about the dating prospects in her classes. She called them all "little nerds and anime boys... no offense". I could have told her for the thousandth time that, actually no, I don't watch much anime at all, but I got her point. I was kind of a nerd, I was more than a little effeminate, and I guess the anime thing just came with the territory.

Natalie wasn't all that much better (which maybe should have been obvious from the fact that we were both sitting here alone on a Saturday night). Her appearance didn't give any nerdy clues -- just that of a typical early 20s black woman -- but every time she talked it was like she thought the words would get away from her if she didn't sprint through a sentence. And if she thought you would have anything to say in response, those sentences could be quite profound; whether about astronomy, sex, politics, or numerous others, her mind could work a topic. It was a task just to keep up with her, and the few people who stayed around her showed that.

But I'm getting way ahead of myself. Somehow the topic of conversation this night moved on to a guy Natalie had been seeing the past few weeks. I thought he was just 'fine' but Natalie seemed to be really into him. She talked about how he was so open and caring and -- you get the idea.

Then she started prying into what I was into and unfortunately that half-bottle of wine betrayed me. I ended up telling her way too many of my fantasies: submission, exhibition, feminization; and all I got in return was that she was "probably a dominant" and "into vanilla stuff". So much for a fair trade of information.

To be fair, I'm not ashamed of who I am. Start telling people you like girly things and you quickly get used to people reacting worse than getting quiet. And I don't think anything I said shocked her too much because I'd been wearing cute outfits around the house, and when I felt really brave I picked a crop-top for a night out.

I held myself differently from most boys: walking with a little more spring and sway, growing my hair out, and shaving the god-forsaken hair off my body -- small things, but they felt fulfilling in some way. But am I a girl? Nah, too much work; plus, I like pockets. I know there are a million and one terms for me. Honestly, I just want to feel cute. Call me a femboy, if you want.

I decided to follow Natalie's instructions, with a small twitch in my loins from equal parts excitement, arousal, and true fear. I made my way to my dresser and realized with a blush that no one had ever seen me in panties before. I had collected a few pairs but I was definitely too embarrassed to be seen in most of them. I decided on a pair of simple, black, hipster-cut panties, my first-purchased and most modest pair. Natalie told me to put on a bra too but I didn't actually own any, thinking the femboy trend of wearing an empty bra more sad than anything. What I had instead was this grey cotton tankbra that I loved.

I looked down at my body before stepping into the shower. Whether or not I called myself a femboy, I definitely had the body for it: ruthlessly skinny and fit enough to have shape but definitely not enough to impress with muscle. I had shaved and moisturized my body yesterday so my skin was still a smooth and unblemished warm-beige.

My shower was uneventful. I would be lying if I said I didn't think about doing a little self-pleasure, but it didn't feel right and I never liked masturbating in the shower anyway. I got out, dried off, and slipped the panties on, checking out the view in the mirror. They may have been more-or-less normal on a girl, but on me they stood out lewdly just by virtue of being panties. I adjusted everything as well as I could and then slid the tankbra over my head. It had the option of tying a cute bow in front so I did that too, figuring I would follow Natalie's "cute" instruction as much as possible, and "slutty" as least as possible.

Our flat was weird: a tiny private bathroom and an oversized single bedroom was shared between us, and two more units plus a kitchen and living area adjoined, making four people in the unit total. So you can imagine my trepidation as I crept into our shared bedroom, even with the blinds pulled and the bedroom door locked. I heard some muffled noises from the common room, but it wasn't anything out of the ordinary.

Natalie had said to just wear the bra and panties, but I figured I should dress to impress, so I pulled out a choker that I hadn't worn out before and quickly slipped it on. Some cutesy socks would have completed the look, but I didn't have any, so I pulled a blanket around myself and sat on the bed before shooting Natalie a text, "alright bud I did what you asked. what's your big plan here?"

"don't call me bud bitch"

And then I heard a sound at the bedroom door -- "THUD THUD THUD". I jumped off the bed at the sound, nearly leaping straight out of my skin at the thought of being seen like this. Somehow I managed not to let out a yelp, but only just.

"Ay, unlock the door. This is part of your surprise," I heard Natalie say impatiently, putting a teasing sweetness on the word 'surprise'.

Letting Natalie in put my senses on edge, but in honesty I had expected her to play this game in person, so I wasn't too surprised. As I turned the lock I suddenly overcame my surprise and instead became conscious of my immodest position so I called out, "Okay but wai---"

And then the door handle immediately turned and within one second I was in full sprint back to the safety of my bed and the modesty of my blanket. Yeah, leaving the blanket on my bed was a dumbass mistake but I really didn't expect Natalie to be so bold. I wrapped myself back up and turned to her with a blush. I wasn't sure if she had seen anything, but she definitely had a smirk on her face and the idea that she was so enjoying me being so flustered was humiliating enough. Thankfully, she quickly shut the door behind her.

"Don't worry I only got a peek, but damn--" she made a face of hedonistic approval "--I think you'll do just fine."

"Fuck you Nat, I was telling you to wait."

"Ahh don't worry about it; there's a reason you're in those panties."

She sat down next to me on the bed and patted my (securely blanket-covered) thigh. I knew she was honest when she said I wasn't her type and nothing was going to happen between us, but goddamn she could be a tease sometimes.

Natalie continued, "Okay, I brought some friends with me. You remember Yana?"

I did, in fact, remember Yana. Natalie and I were both in an "Engineering Ethics" class this semester. The class sucked badly, but a significant part of the class involved a small group we'd keep throughout the semester: consisting of Natalie, Yana, and I. I didn't want to know how my classroom acquaintance was going to factor into this particular event, but Natalie didn't hesitate to tell me.

"She's here and I also brought over this guy I met in the hall a few weeks ago and they're hitting it off in the living room right now."

I was getting more anxious. "Nat, why are they here?"

"For you, silly," she said as if it was the most obvious thing in the world, "here let me go get them."

I was not ready for that yet. "Whoa, you're not bringing them in here. I think you need to tell me what's going on."

"Nuh-uh, I'm not telling you shit. You just have to trust me on this one. That's the only way it works."

I scanned her face. Her eyes were piercing, clearly following some kind of script in her mind and interested in seeing how I reacted to it. She did this sometimes; manipulating people, but somehow for their own gain. Like she could see what you really desired and was addicted to unlocking it. I'd learned to sit back and watch her work most of the time, but no information at all definitely wasn't good enough for me this time.

"Uhh, I have no idea what's happening. How do you think you would feel in my situation?"

She thought for a second before coming up with a solution. "Okay fine. I know you're going to enjoy this, but if you don't just say stop and, as payment, you can do to me whatever I did to you."

This sounded better to me; an insurance plan, if you will. "Everything you did to me, including anything with our friends here?" I said, gesturing to the living room.

"The very same. BUT, only if you actually aren't enjoying it, and I'll know you if you are, you cunning little bitch," she said. "If you use this to double-cross me you know you'll have hell to pay."

I sighed. It seemed reasonable. She really couldn't do anything to me that she would hate herself, and I knew she would keep her word. "You're the cunning little bitch. I don't know how you always get me to trust you."

"Ahahaha --" she had a shitty evil villain laugh "-- time to bring in our guests."

And she did. For my part I readjusted my blanket to make sure it would appear that I was chilly instead of half nude. My hastily crafted plan was to shrug them off. This was my room after all, and I didn't have to play into Natalie's games. I told myself that she was just pulling a little prank on me: get me indisposed, invite some friends over, and then she would giggle at me with them being none the wiser. We would all be hanging out under normal pretenses soon.

Nonetheless, I did feel shaky as they all entered. I realized I had to greet them somehow or it would be even more awkward, so I muttered out an aloof, "Hey guys, you going somewhere?"

Natalie gave me a look. "Ha-ha Orlo, I told you they're here for you."

Yana and the boy (whose name I didn't even know) gave each other a look that told me they also didn't know what they had walked into. The awkwardness was almost palpable.

"Okay, let's try this again. Orlo, this is Aaron. He's a literature major and he lives a bit down the hall. Obviously that's Yana, and they both know about you already," Natalie said with a wink.

"Hiya," I said to the pair, and deciding to challenge Natalie directly on this one I said to her, "So they're here for me, are they?"

She could barely contain her smile. It was obvious she was really looking forward to this, and that gave me the worst feeling so far. "I may have let it slip that you're a little pervert who has a certain outfit you want to show them today, and isn't that right?"

Yeah, my heart sank. She told them I was a pervert? She was suggesting that I get up and prance around in my bralette and panties in front of these people? How would I be able to look Yana in the eyes again? What if I met Aaron in the halls?

I broke out into bona fide laughter. "Fuck you Natalie, no way."

"You said you trusted me, Orlo. You do trust me and you aren't going back on this one."

Natalie and I had been living together for a semester and a half, but we had an unspoken pact to avoid awkwardness in a mixed-sex dorm. I guess you'd call me modest because Natalie had never even seen a glance of me in my underwear. I hadn't thought about it specifically, but I always changed in the bathroom, slept clothed, etc., so this was doubly out of my realm. Natalie wasn't as careful, but we both knew not to perv out on eachother.

Yana and Aaron looked like they wanted out of this situation immediately. Aaron was the first to speak up, saying, "Maybe there's been some kind of mistake?"

"Nope, no mistake," Natalie said. "I know we all want this to happen, so it's up to you, Orlo. Break free from your inhibitions."

No one knew how to respond to that, so Yana jumped in, "Okay, well, you could show us whatever you want but also I don't want him to feel pressured."

She was clearly avoiding eye contact with me. Natalie had been teasing me the past few weeks that Yana had a crush on me and I thought she was entirely joking until this moment.

I glanced over at Aaron and he looked a little on edge, but nonetheless ready for whatever was going to happen next. Natalie sure did know how to pick 'em

So I took one more moment to think about it before looking them both in the eyes and saying, "You're sure you're okay with this?"

Aaron gave a, "Yeh, just some fun right?" and Yana gave a simple but sweet, "Sure".

I guess that was more-or-less what I needed to hear. I still don't know why I did it, exactly. Partially, it felt like a challenge from Natalie and I've always been a slut for a challenge. But most of all I wanted to know whether I really would enjoy it (as Natalie seemed so sure), and I knew another opportunity like this wasn't going to come around any time soon.

I shook my head at how absurd the whole situation was and then, looking down at my blanket, realized that I had absolutely no idea what I was doing. I hadn't ever modeled -- the closest thing was a seldom few risque pictures I had taken in a bathroom mirror. Do I just rip the band-aid off or are they expecting something more? Shyness took over me again, this time as much about performance as modesty.

Luckily Natalie 'came to the rescue' once again. She strolled right up to where I was sitting until we were almost touching.

Surprisingly softly she said, "Here, let me help you with that." And she carefully grabbed one end of the blanket.

I dropped my hands, looked at the floor, and froze. It turned out that I was filling out my submissive archetype pretty well. Natalie went agonizingly slowly as she pulled my covering apart, making a show and looking like she was unwrapping a present. I blushed a hard cardinal red as I felt the coolness of my skin's exposure to the air; first my shoulders and bra, down my stomach, panties, then my thighs, and finally my calves and back as she pulled the blanket completely off and threw it beside me on my bed.

I glanced up and I'm not sure which sightline was more embarrassing: Yana and Aarons' straight at my cock or Natalie's straight into my eyes. I quickly glanced back at the floor because I was not going to maintain eye contact with any of them in this state of dress.

I had become much more aware of my panties as they were exposed, wrapped softly but tightly around my cock. I could imagine the view they were getting, and it was in my peripheral vision anyway. Helping my modesty was the black color of the material, but it was stretched tightly enough that my intimate anatomy was pretty well inferrable. I was hanging sideways at a 45 degree angle, an otherwise smooth shaft ending in the obvious bump of the crown. If they looked closely at the spot a little lower they would see the bubble of my pouch too. Overall I felt pretty damn exposed, and I just barely resisted the urge to snap my hand down there and turn away shyly.

"You should see your blush," Natalie teased, saying it under her breath but clearly intending everyone to hear it.

The feeling of their stares kept growing in awkwardness, so eventually I said, "Okay, you've had your fun now give me that back," reaching for the blanket.

"Nope, I think we're going to take a good long look," she responded. "And how could we not with that lovely tum beaming at us." She continued describing my body as if she was a carny and I was some deranged carnival act, "On the lower half those silky-smooth thighs and especially those gorgeous panties."

"We get it Natalie, you're a huge pervert," I shot back, feeling overwhelmed by her explicit cataloging of my body parts.

"True, true, but I'm not the only one. Yana, don't you think he looks just delectable in those panties?"

I chanced a look up at Yana and she had clearly lost some of her apprehension from earlier. I caught her stealing an extended glance at my panties (again!), so she bashfully backed out of perving over me.

"Err, honestly yeah he does," Yana said, the last word coming out more as a giggling exhale.

At this point I was getting a little worked up. Natalie's shameless descriptions started it, and having Yana vocalize her lust amplified it a lot. Natalie was right: I was an exhibitionist, and having three sets of eyes clearly enjoying what they were seeing would turn me on no matter how I tried to control it. I was trying pretty damn hard not to get erect in front of them, but of course that avoidance was only making it harder.

"Do you think he would show us the rear?" Aaron questioned shyly.

I cocked my head to the side in half-mock frustration.

"Oh would he?" Natalie ask-commanded, doing the 'turn' gesture with her fingers.

"Oh my god you all are killing me. I'll leave if you need to rub one out," I said, and then immediately regretted it because of the new image that popped into my head: walking out into the living room dressed like this. Luckily none of them jumped on that idea, and the room was silent as I turned around and presented my ass for the first time. This was also a blessing because it allowed me to momentarily hide the erection that was starting to boil up.

My panties were almost full coverage, so only the very bottom part of my asscheeks peeked out of their black encasing. I would love to have a more endowed asset, but I'm at least naturally athletic enough that what is there has a nice shape, and I've been told it's cute before. My back was much the same story: the muscle could be easily made out, but its nature was more willowy and lithe than strong. Finally, my waist curved out gently, complementing the level strength of my torso with just a bit of extra flair. I put one hand on my hip and leaned slightly to that side, trying to imagine I was at a benign modeling gig.

I looked down at my penis and the problem there was not going away. The panties were cut a lot lower than boy's underwear in front, so I was faced with the new fear that if it kept growing it might sneak right out of its attire. I snuck in a quick adjustment to help ensure that wouldn't happen.

"Thanks Orlo. I have to admit this is pretty fun," Aaron said. I had figured that Aaron was attracted to me -- otherwise he wouldn't be here -- and that confirmed it.

"Hey Orlo, now that you're getting into it, do you want to be touched?" Natalie asked.

That wasn't the question I was expecting. "What, you perverts want to get your hands all over me?" I shot over my shoulder.