The RA From Hell

This is a story from my freshman year at college, where despite being an ordinary straight guy, I somehow managed to lose my virginity to another straight guy.

I went to college a fair distance from home, so when I arrived I only knew a couple people at the school. The people I did know were merely acquaintances too, so it's safe to say I didn't have any real friends going in. As a result, I got randomly matched up with my roommate, and his name was Rob.

I got along great with Rob, even from the very beginning. I could tell he came from a cooler crowd than I did in high school, but he always came across as a pretty nice guy. It didn't take long for me to see firsthand that he had no problem getting girls either, as the first weekend we were there he hooked up with someone in our room. He was perfectly nice about it, as he pulled me aside beforehand to ask if it was ok if they had the room for an hour or two. Of course I wasn't going to say no, and it was an enlightening experience seeing how easy he made it look.

After that weekend, he made it clear that anytime I needed the room, to just give him the word and he'd clear out. I kind of laughed and mentioned that I'd love to take him up on that offer but he shouldn't hold his breath. I admitted to Rob that I was a virgin, but he was totally cool about it and made it clear that I shouldn't sweat it. He then said that if I was up for it, he would make sure I got plenty of action this upcoming year. Between his confidence in me, and it being a whole new world at college, I definitely thought it was possible.

The first few months went by and despite my initial optimism, I hadn't hooked up with anyone yet. Perhaps one of the reasons why was I had developed a huge crush on a girl in our dorm, Margo. My feelings for Margo pretty much killed my interest in having a random hookup with anyone else, but the problem was it was becoming clearer and clearer that I wasn't going to be hooking up with Margo either. It was blatantly obvious that she was solely interested in being friends.

The two of us actually hung out quite a bit, but a lot of it was school related. She was pre-med and I was studying electrical engineering, so we both ended up in the same intro to chemistry class. Since we were in the same dorm, we ended up working and studying together a ton for this common class, and I loved every second of it. But it wasn't all studying and homework, as we both lived on the third floor of the dorm so we'd socialize a fair amount just casually hanging around people's rooms as well.

Margo was smart, super sweet, and in my opinion absolutely beautiful. She had straight brown hair, a petite cute body, and just the most amazing smile. I'm sure it had to do with the amount of time we spent studying together, but apparently it was obvious to everyone around that I had a huge crush on her. At one point, Rob had even mentioned that of all the girls in our dorm, the one he was least likely to ever hook up with was Margo. He then clarified that Margo was totally hot, but that he could never do anything with her just because of how I felt.

So it was safe to say that seemingly everyone in our dorm knew of my feelings for her, and I'm sure that meant Margo knew too. Rob and I had discussed what approach I could take, and he kept pushing me to just man up and ask her out on a traditional date. He admitted though the odds were pretty high that she'd give me some sort of classic excuse about wanting to "just be friends", but he believed it was worth a shot. What stopped me though, was I always figured that she had to know I liked her, and if she was at all interested she would've given off some sort of sign. So despite Rob's insistence that I had nothing to lose, I just kept the status quo alive and didn't ever ask her out.

So while my sex life was non-existent, of course I still masturbated a ton. Most of the time I'd just wait until I knew Rob was out of the room for awhile and I'd jerk off to internet porn. Sometimes I would find myself horny at night while lying in bed, and if I could hear that Rob was definitely asleep (based on his breathing), I'd close my eyes and fantasize about Margo while lying in my bed, and silently relieve myself into a sock. Sometimes I'd specifically wear socks to bed just so I could take them off and use one of them to cum into if the opportunity arose. I felt kind of bad jerking off with my roommate right there in the same room, but I always tried to make absolutely sure he was asleep before ever attempting it.

So that was the state of my life in terms of sex. Lots of jerking off, a huge crush on a girl that I wasn't willing to risk doing anything about, and very little interest in pursuing anyone else not named Margo. And then one random Tuesday afternoon, everything changed.

Rob came busting through the door while I was just sitting on my bed playing a game on my phone.

"Good. You're here." He said, kind of in a panic.

"Yeah, why?" I responded. "What's up?"

Rob continued on, "Dude. You know Vicki? The RA?" RA stood for Resident Advisor, and they were basically like the students in charge of policing the dorm. I use the term policing very lightly though as most RA's weren't much for actually enforcing the rules. Vicki was the RA on the girls' side of our floor, and like all RA's, she was a couple years older than us. Our dorm had three floors, and each floor was basically half guy rooms, half girl rooms, with a dividing line down the middle. Each side of every floor had an RA (so one guy and one girl per floor), and they lived in the only single rooms in the dorm, so they didn't have roommates.

"Yeah, of course I know Vicki."

Rob then goes, "That girl is a freeeeeeak!" With a super exaggerated pronunciation of the work 'freak'.

"Why? What? Did you hook up with her?" I asked, legitimately confused. Vicki had a pretty edgy look to her, and while she wasn't unattractive, she certainly didn't look like the type of girl Rob would normally go for.

"No. Not really. Well... no." Rob answers my inquiry with a completely weird response that leaves me even more confused as to what he's all worked up about. "Forget that." He continues on.

"What the fuck are you talking about?" I ask starting to get annoyed.

"Dude, just come with me." He motions and opens the door so we can head out. "Are you free? Do you have class?"

"Yeah I'm free, I don't have class the rest of the day." I say as I slowly get up and head towards the door.

Rob and I head out and start walking down the hall. "So where are we going?" I ask.

"Vicki's room. You have to see this." He says adding to the mystery of what the fuck has him all worked up.

So we continue down the hall. We pass the guys' bathroom, then the common lounge area that divides the guy and the girl sides, then the girls' bathroom. Finally, all the way at the end of the girl side of the hall is the RA's room belonging to Vicki.

Rob gives her door a couple of quick knocks and we hear "It's open!" from inside the room. Rob opens the door and we both walk in.

"Hey boys..." Vicki says with kind of a sly, mischievous, undertone.

Rob doesn't say anything immediately, but I say "Hey, Vicki."

Rob seems singularly focused and heads straight to Vicki's computer on her desk. I'd say 95% of students here have a laptop as their main computer, but for whatever reason Vicki has a full blown iMac. It's the big one too, so it has like a 30" screen and takes up practically her whole desk.

"Can I show him?" Rob asks Vicki, still seemingly in a breathless hurry.

"Sure, go right ahead." Vicki responds. And then she adds, "The folder should be minimized if you wanna bring it back up."

And with that Rob pulls out the desk chair slightly, motions to me and says, "Here, have a seat."

I sit down at Vicki's computer and Rob finds whatever this minimized folder on Vicki's Mac is and clicks to bring it back up on her desktop. With the folder expanded, I can see it seems to have a bunch of sub folders and each one is a person's name. The first thing I notice is that all the names are female. They appear to be in alphabetical order and the first four I see are Alissa, Beth, Evie, and Hillary. It's at this point I realize that all the names are girls here on the third floor of our dorm. Alissa, in fact, is Margo's roommate.

"What is this?" I ask looking at both of them confused. "What are these files?"

"Dude, just pick a name and open it up." Rob instructs me. "You'll see."

"Ok." I say, but I'm starting to get pretty weirded out now. My best guess is it's some sort of disciplinary info that Vicki has on them as their RA? But that doesn't make much sense for any number of reasons. Regardless, I click on the first folder, 'Alissa', and open it up. In the sub folder there appear to be two files, and they look like they're videos as they're both.mp4 files and show the play button on their icon.

"Movies?" I ask even though they obviously are.

"Click it." Rob responds.

So I go ahead and double-click the first video file. QuickPlayer opens up, taking up most of the screen, and the video starts with a view of a shower head and what looks like an empty shower stall. It actually looks just like our dorm showers, except reversed like a mirror image. And then I see a hand come into view that opens up the shower curtain and it all dawns on me. Holy fuck, this is a video from the bathroom showers in our dorm. It looks reversed because it's from the girls' bathroom, and I'm used to the guys' bathroom which must have a mirrored layout.

"Oh my god." Is the only thing that comes out of my mouth as the hand reaches in and turns on the water. A few seconds later, the person comes into view and it's clearly Alissa, Margo's roommate. She closes the shower curtain behind her, and then turns so she's facing the camera with the shower head behind her.

"You have video of people in the shower???" I ask as I look back at Vicki. She gives me a nod but doesn't say anything. I have no idea what to think and am completely overwhelmed by this whole turn of events.

Still with my back to the video playing on the computer, I turn to Rob and he kind of silently mouths the word "freak" to me without Vicki being able to see. I look back at Vicki again and ask, "So you filmed them?? You did this?"

"Do you like it?" She says as she answered my questions with her own.

I don't answer her but instead turn back around and look at the video again. Alissa has shampoo in her hair and is rubbing it in. She has shorter dirty blonde hair which is covered in suds right now. Her tits are naked as can be and are bouncing around as she raises her hands up to wash her hair. Her pale white body is completely visible all the way down well past her pussy. I can see she has a decent patch of pubic hair, but the resolution is good enough I can even make out the details of her pussy lips. It's clearly an HD camera that was used to record this, and the video has one of those slight fisheye lens looks to it so it also shows a pretty full view of the shower stall. I continue to watch and Alissa keeps going about her business, seemingly without the slightest idea she's being recorded.

I'm completely confused and turned on all at once. Why would Vicki record people in the shower? Why would she show us? This is a huge fucking deal. And she's their RA, so she's supposed to be the person looking out for them, not violating them like this.

I reach up to the mouse and drag the bar to fast forwarded through the movie. It goes on for like 10 minutes and then ends, so I close that one. I then click the second video file in the Alissa folder and it's another very similar movie, but from a different time. I close that one quickly after seeing it was more of the same.

I go back one level and click on the Hillary folder. There's only one movie in there and I click it. It starts and Hillary enters the shower completely naked but I can see her leave her towel on the hook just outside the stall. Hillary is a cute Asian girl, Korean I think, with long, straight, black hair. She starts taking her shower and the water comes running down her body, over her gorgeous small tits. She has these beautiful, long dark nipples I never would've known were there, but they look amazing as the water runs over them. Her pussy is bald as can be and I can't look away from it. The fact that I know this girl and get to see her naked is such a turn on. I've seen plenty of porn before, but before today I had never both known someone and seen them naked. After a couple of minutes of me silently watching and neither Rob nor Vicki saying a word, I fast forward Hillary's video and get to the end. I close it and again go back one level to where all the named folders are. I take a pause and just sit there trying to collect my thoughts. It's pointless though as my mind is racing.

"Scroll down." Rob then says to me.

I increase the size of the finder window to where I can see a bunch more names now. After I do this, Rob takes his finger and taps like three times directly on the screen. "This is for you." He says emphatically, as he taps right on the sub folder called 'Margo'.

"Don't fucking touch my screen." Vicki interrupts to scold Rob for potentially leaving fingerprints on her computer.

"Oh, my bad." Rob quickly apologizes and then uses his sleeve to make a half-assed attempt to clean any mark he left. I can't help but make a mental note of how aggressively Vicki scolded him, as it seemed kind of odd.

I return my focus to the movie files, and there's simply no way I could resist clicking on Margo's folder, so I open it up. The thought obviously had crossed my mind that there would be videos of her as soon as I realized what Vicki had here. But for whatever reason, I didn't want to appear like I was most concerned with seeing the Margo videos, even though I certainly was. After opening up the subfolder, I see there are two files in hers. I was pretty nervous watching the videos of Alissa and Hillary because I realized how wrong all of this is, but now that I was staring at potentially two naked videos of Margo, my nervousness level went through the roof.

My heart was racing and beating so loudly I could literally feel it in my throat. I had no idea if the other two could tell I was this worked up, but I was able to gather myself enough to go ahead and click the first video so it started to play. It began just like the other two with an empty shower, and then about five seconds in I see Margo enter with her back to the camera. I can't even see her face yet and It's literally the most beautiful sight I have ever seen in my life. She appears to be waiting for the water to warm up, and in the interim is just standing there, giving me a view of her gorgeous naked ass. Her tiny butt looks so soft, round, and petite, it's just the cutest thing imaginable. I can't help but wonder what her frontside must look like, as I anxiously await for her to turn around.

"Dude, what do you think?" Rob interrupts before I can even fully process what I'm seeing, and what I'm about to see when she actually starts showering.

"She's beautiful." I say quietly.

"I know. After watching her videos I knew I had to show you!" Rob explains. I go back to just focusing on what's in front of me when Rob then says, "Alright, I'll leave you two here. Pleasure as always, Vicki." And then he abruptly lets himself out of the room and leaves just me, Vicki, and an unbelievably naked Margo on Vicki's computer.

I was about to go back to watching Margo shower, but now that it was just Vicki and me I felt like I had to get an explanation. So I actually decide to delay the pleasure that's about to unfold and instead pause the video. I need to make sense of some things first, and so I turn to Vicki and say, "So how did you record these???"

"Ha." She responds, and then coyly adds "A magician never reveals her secrets."

"So you've just been recording everyone on our floor? Like all year so far?" I ask.

"Something like that. Let's just say it's a hobby of mine." She answers.

"And who all knows about it?" I continue with the questions.

"Just you two. That's it."

When she said that I think I gave kind of a confused face as to why us, and then Vicki added quite sternly, "And if you tell anyone else, I'll fucking kill you."

It was clear when she said it that she wasn't joking. Well maybe she wouldn't be capable of murdering one of us, but it was pretty damn clear we shouldn't tell anyone. Either way, it was safe to say I was quite intimidated by her.

"So why us?" I ask as I still just don't get it.

"It was actually just Rob that I wanted to show." She starts to explain. "In case you can't tell, I kind of have a thing for him, so I decided to show him my collection. He's the one that kept begging me to show you."

"Really?" I ask somewhat rhetorically. But then I realize it was probably all about Margo. I'm guessing he just really wanted me to get a chance to see her naked, no matter how fucked up this whole thing was.

Vicki then continued, "I don't want everyone knowing, but I figured if you guys were roommates it wasn't a big deal to bring you in on the secret as well."

With that it all started to make a little bit of sense. Not the part about Vicki secretly recording these girls in the first place, that part is still so fucking random and psychotic. But I get why Rob and I would be the only ones to know at this point. So finally, I turn back around to where the Margo movie is paused, and I figure if I've come this far, I can't possibly leave without watching this video.

As I'm about to hit play and resume watching, Vicki interjects. "I'll tell you what..." She starts. "I'll give you the same deal I gave Rob."

I look at her, but don't say anything.

She continues, "In case you were wondering, these videos won't ever leave this room, but you are welcomed to jack off to them right here."

"Are you serious?" I respond, not sure what to make of this offer.

"Yep. Rob's already performed multiple times for me."

"Oh, you'd be watching me while I did this?" I ask as I hadn't thought of that aspect when she first offered.

"Damn straight." She confirms. "And you have to get naked for me."

What the absolute fuck is going on I think to myself. All I can think of is Rob mouthing the word 'freak' as that's clearly what this Vicki girl is. I just sit and ponder my options here.

I'm not going to lie, I found the idea of a girl seeing me naked and watching me touch myself to be quite enticing. I've literally done nothing sexually with another person before and this would be a pretty thrilling experience. And then I think about how hard I'd cum to a video of Margo that I've still only gotten a glimpse of, but I'm sure is the sexiest thing I will ever see in my life.

Then my mind takes it one step further and thinks, maybe there's a chance Vicki will join in and *help* me once I get started? Maybe I'll get a blow job? Vicki certainly wasn't my type, but that would be pretty wild. She had dyed blue and green streaks in her hair to go along with a ton of ear piercings, a nose piercing, and who knows what other hidden piercings. She had an athletic body with some serious muscle tone, but overall her look was just too edgy or alternative for my taste. Margo was kind of the opposite, as she was a cute, sweet, girl next door type. That's the look that's always done it for me pretty much my whole life.

In the moment though, considering I was horny as fuck, the idea of fooling around with Vicki was certainly appealing. I took one more look at the paused video with a naked Margo, then turned and looked at Vicki, and said "Ok, I'm game."

I stood up, took off my shirt, and then followed by unbuckling my jeans and pulling them down with my boxers. As I do this, I ask Vicki, "Do you mind locking the door?"