The RA From Hell

Rob and I return to our discussion and he says, "So we're really fucking doing this?"

I tell him, "I think it's clearly the lesser of two evils. I just can't get kicked out of school. Like, I CAN'T"

Rob agrees, "I know. My parents would literally kick me out of the house. I'd have nowhere to live." And then he continues, "Look, this whole thing is going to be fucking stupid. We just humor her, get this shit over with, delete those fucking files, and then one day we'll look back at this and laugh. Or more likely we just never speak of it again."

"Ok." I say.

Rob then turns to Vicki and says, "Ok, you win. We'll do option two."

"Fantastic!" Vick exclaims as she joyfully claps her hands. She then says with a big smile, "Why don't you two get started by getting naked."

"Woah, hold on." I interrupt. "No way we're doing it here. That would be insane with all your hidden cameras. If we're going to do this it has to be in our room, AND we get to make sure you're not bringing any of your magic recording devices into the room."

"Oh fuck yeah." Rob agrees wholeheartedly. "Great fucking call."

"Ok, that's fine." Vicki says, and then proceeds to hold up her arms as if she's ready to being patted down right now. "Or you wanna walk over and then you can pat me down when we get there?" She says.

"That works." Rob says. And with that the three of us head down the hallway to our room. Rob and I don't say a word as we're clearly processing what's about to happen. Vicki, on the other hand, is excited as can be at the prospect of the show she's about to watch. When we get to our room, we let ourselves in and lock the door behind us.

Vicki walks into the room, raises her arms in the air and says, "Hidden camera check?"

Obviously the chances of her somehow having a smuggled camera were pretty low, but given her history, it was still worth checking. Rob walks over to her, pats her sides, checks her pockets, and then admits that there's nothing there. If nothing else, we're now at least confident that whatever is about to go down won't end up being recorded. But that was probably the only silver lining in our minds.

"Ok, boys, time to get naked." Vicki starts over again with her instructions.

We both accept the fact that this is just how it's going to be and start undressing without saying a word. Having already gotten naked in front of Vicki once, it didn't seem like that big of a deal. It was definitely weirder having Rob there too, though. He and I quickly get undressed as we're clearly not trying to draw anything out and we want this whole fiasco to be done with as soon as possible. I step out of my pants and am now standing there totally nude and then I see Rob does the same.

The first thing that catches my attention though doesn't have anything to do with Vicki or how she's watching us, it's Rob's penis. I immediately notice that it's uncircumcised, which is interesting because I hadn't noticed that in either of the blackmail videos where he was jerking off. But now that he's just standing there with his dick out in plain sight, all I can see is his foreskin. I feel like most of the cocks I see in porn are circumcised, and I've never seen another penis of any kind in real life up close, so I simply haven't seen many that looked like this, and it caught me off guard.

That wasn't the only difference between our two cocks either. I'm sure it had to do with Rob having significant sexual experience, but his was clearly as soft as can be, while I was paranoid that I was going to be way harder. When I got undressed, thankfully I didn't have a full on boner, but I was definitely feeling some sexual nervousness that was making me semi hard. Maybe Rob thought I was soft and just had a huge dick? Doubtful, but I was definitely worried that he was going to be soft this whole time and I was going to be erect, making me look like an idiot who can't control his cock.

"Wow, look at you two." Vicki comments. "Your dicks look sooooo different."

"You've already seen both of them." Rob points out in a clearly annoyed tone. While I'm going through this experience pretty wide-eyed and shell shocked, Rob seems downright pissed off.

"I know..." Vicki responds. "but never side-by-side like this. Ok, I want you guys to stand next to each other and hold each other's dicks in your hand."

"Fuck." Rob very quietly mutters under his breath.

But we do as we're told and position ourselves across from one another. Neither one of us wants to make eye contact so we look down, left, right, or basically any direction except straight ahead. I reach out first and I just kind of touch Rob's soft cock with my thumb and index finger trying to make as little contact as possible. Rob follows suit and does something similar to mine.

"Hmmm..." Vicki says as she comes over really close to inspect our hands on cocks. "I can see one of you is having a little performance anxiety and one of you isn't."

I assume that's a comment about Rob being totally soft, but maybe she actually means I'm just nervous? I really don't know.

"Hold his whole dick in your hand." Vicki instructs Rob in regards to my penis. And so he does as he's told, and with my partial erection there's enough shaft for him to do that. Soon enough he's actually holding my cock with his whole hand. Despite the fact that it's a guy doing it, I can't help but get aroused by the feeing as it's the first time my penis has ever been held by another person.

"Jack him a little bit." Vicki now tells Rob.

Rob doesn't bother complaining and instead just silently does as he's told. He starts jerking me up and down rather gently, but this takes my partial erection and turns it into a complete, fully-extended hard on. I'm now totally erect and getting jerked off by my roommate. I definitely can't look at Rob and I don't really want to look at Vicki either so I just kind of stare off into the corner of the room. There's no doubt it feels good though. The sensation is obviously very similar to when I would jerk off, but having it done by someone else adds a whole wrinkle of unpredictability and excitement. At one point I even close my eyes and focus on actually enjoying this experience.

Vicki must've noticed that it was actually feeling good to me, because she blurts out to I assume me and not Rob, "Are you gay?"

Before she barely even finishes her question though, Rob immediately responds for me. "He's not gay. He's a virgin."

"Ahhhhhh." Vicki goes.

"I'm pretty sure this is the first time anyone has ever touched his wee wee." Rob explains and jokes all at once.

"That's ok. This is all starting to make sense then." Vicki says, and then she continues. "Nice. This is good. You're both off to a good start." Rob doesn't say anything else and I don't either. "But we're just getting started." Vicki adds with her happy and mischievous tone that she's had this whole time.

She then takes Rob's hand and removes it from my cock. Then Vicki takes my hand and leads me over to my bed that's perpendicular to the wall in our room.

"Up on the bed." She tells me.

I don't say a word but continue to do as I'm told. The fact that she was in charge and I wasn't, probably helped make this whole experience easier on me. I kind of had the mindset of just do as you're told and everything will be fine in the end. Without any decisions to make, it didn't actually feel that stressful, ironically enough.

The dorm beds aren't very high off the ground but I climb up on it like I'm told.

"Turn over onto your knees." Vicki now says, which I assume she means like in a doggy-style position. When she says this, I do it, but it really stepped up the nerves for me. Holy shit I think, this is about to get a lot more intense, no matter what she has planned.

At this point, I should probably mention that I have experimented on my own with sticking things in my butt before. I've never actually stuck anything very big up my ass though, it's mostly just been skinny objects like a pencil or ballpoint pen. I'd slide them in and then leave them there while I jerked off. Then at the end, I would either pull them out with my hand or sometimes I would enjoy trying to push them out on my own. I didn't do this too often, but I had experimented enough that the thought of something in my ass wasn't too intimidating on its own, but I was worried that having anything significantly larger than a pen wouldn't be nearly as comfortable.

Anyway, I get on my hands and knees on the bed, and Vicki immediately comes over to adjust my position herself. She puts her hand on my upper back and guides me down towards the bed so my torso is resting on the mattress while my head is turned to the side, also on the bed. I'm near the bottom of the bed so my head isn't on a pillow or anything and my feet are resting against the bottom part of the bed frame. While my upper body is down on the bed, I'm still on my knees so my ass is up in the air. Vicki then takes her hands and spreads my legs apart at the thighs to open me up even more.

I am now completely exposed. My head is down so I can't see behind me, but I can feel how my ass is totally spread open and I'm sure giving the two of them a view of everything. I can even feel a slight breeze of cool air on my asshole. Again, I feel like I've surrendered all control and decision making here, so I'm content to just do as I'm told. And to be honest, being on display like this, and getting looked at by not one, but two people, is highly erotic. My cock is still rock hard. I am nervous though about what is going to happen next.

"This is going to be a problem, isn't it." I hear Vicki say, not sure what she's referring to.

"Yeah, I told you." Rob responds.

"Does this help?" Vicki then asks.

I can't see anything that's going on behind me so I'm trying to make sense of it. I hear a little noise and then I realize she's trying to jerk him off a little. I can only assume the problem she's referring to is that he's too soft for whatever Vicki has planned, and considering I'm on the bed with my asshole spread wide open, it's a safe bet she's going to want him to fuck me.

"New plan." Vick says as it sounds like she stops jerking him. "Try fingering him first."

I hear that and my heart skips a beat. A few seconds go by but then I feel a touch directly on my asshole. It's a gentle touch as it stays right on the surface for a second. I have to assume it's Rob's finger but I don't actually know, since I can't see them and I have zero desire to turn and look. The feeling is unlike anything I've ever experienced before. It's so exciting and invasive all at once, it's nerve wracking. Plus I'm worried he's going to just plunge his finger deep into my ass any second now without warning. I can't imagine that would feel good so I'm nervous about that.

"Go ahead. Finger him." I hear Vicki say in kind of an impatient tone.

I hear a pretty audible sigh from Rob and then another quiet "Fuck." Under his breath. Then I feel more pressure from Rob's finger as he begins to slowly push it inside me. It's pretty intense and it's definitely weird, but it's not really bad or good, if that makes sense. It doesn't feel like his finger's in that far before I feel him remove it.

"We need something." I hear Rob say. "Like lube, lotion, just something. It's way too dry."

"Yeah, Ok." Vicki agrees. "What do you have?"

"Here let me at least get some hand lotion." Rob says as I hear him get up and walk over to his closet. Even with this minor break in the action, I have no desire to look around or do anything other than keep my current position with my eyes closed.

He comes back over and I hear him place the lotion on the floor. A couple of audible pumps of lotion later and the next thing I know there's a shockingly cold sensation when he initially wipes what seems like a ton of hand lotion on my ass crack. It's cold as shit and also very wet. It's not a great feeling at first for sure. Next, I feel his fingers again and this time they're rubbing up and down and all around my asshole. Soon enough, the whole region is completely lubed up.

No one says anything, but next I feel a finger return to the precipice of my rectum. Rob doesn't seem to waste any time and this time plunges his finger right in. With the lotion, it slides in really easily and goes in much deeper this time too. The feeling absolutely catches me off guard and I let out an involuntary combination of a grunt and a moan.

Rob leaves his finger in me and keeps it relatively still and I'm just trying to process the whole thing. It feels kind of good I guess? Much better than the dry finger tip he initially had in me. I feel very full as there's no doubt his finger is significantly wider than the ballpoint pens I was used to. I have tried fingering myself in the past, but the angle would always be awkward and it was nothing like this situation where I was on all fours and he was coming at me from behind.

"Am I done here?" I then hear Rob ask.

"Use all your fingers. One at a time." Vicki says with a laugh.

And with that I feel Rob's finger leave my ass. It kind of has the sensation of pooping, but a little different. Again, it's not really bad or good, just weird. But then immediately after it leaves, another finger enters and takes its place. Then, that one comes out, and a new one back in. This happens over and over again. At least a dozen times. This sensation of me getting finger fucked starts to grow on me and there's no doubt it feels good. I continue to just lie on the bed head down and motionless, but I'm enjoying each thrust in and out. Then I can't help but have a thought run through my mind. Am I actually gay and didn't know it? Or maybe I'm bi?

I contemplate this pretty major question while getting finger fucked. But then I think about what if it was Vicki fingering me right now and not Rob? And when I think about that, I instantly realize how hot that would be. For just a second, I picture Vicki is the one probing me with each thrust and all of the sudden I feel like I'm building to an orgasm. I snap out of that thought experiment and am brought back to the reality of the fact that it's my roommate, a guy, who is doing this. I assure myself that this must mean I'm straight? And then I come to the acceptance that it's possible to be straight and still enjoy a physical feeling like this on some level. At least that's what I tell myself.

My inner monologue gets abruptly interrupted though when I hear Vicki say, "Ok, try two fingers at once now."

After she says that, I feel Rob remove his finger and not replace it like he had repeatedly been doing before. And then after a delay of maybe ten seconds, I feel a huge push that honesty feels more like five fingers, than two, but I can safely assume was in fact, only two.

It's immediately clear that there's a huge difference between two fingers and one. It literally feels like my sphincter tears as there's a ripping pain that totally overwhelms any other sensation I'm having at the same time. I wince in pain and just try to get through it without letting on how uncomfortable it is. Soon enough, the initial thrust is replaced by more in-and-out action as Rob starts fucking me with his two fingers.

"Nice." I hear Vicki express her approval of the situation. "So hot."

The two finger fucking maybe gets ever so slightly more tolerable as time goes on, but not much. While the one finger probing actually felt kind of good, there's no doubt I'm not enjoying this change in approach. But after only maybe a minute or so, I hear Rob say, "Look." And then he pauses before withdrawing his fingers. "I have to stop."

"Ok, Ok, I see it." Vicki says, which makes me wonder what the fuck happened? What did Rob and Vicki see?

Since Rob was no longer inside me, I can't resist and I turn over and kind of place my hand down by my asshole and look at them and ask, "What is it?" There isn't anything obviously wrong but I'm still kind of freaked out by their reaction.

"It's not a big deal." Rob tries to assure me. "It was just a little bit of blood. You started bleeding."

"Oh shit. Sorry." I instinctively say.

"Don't fucking apologize man. It's her fucking fault." Rob says as he looks at Vicki.

"You'll be fine." Vicki then says in defense of her actions. And then she immediately moves on to what's next, not even giving me a chance to recoup. "Ok, you two switch places, but I want you on your back, not on all fours." She says to Rob.

So I gingery hop off the bed and Rob takes my place and just lies down like someone normally would on a bed. The bed has room on each side except the head, and Vicki walks around to the far side and kneels down on the floor. Then she says to me, "Come sit across from me."

So I do as I'm told and I kneel down next to the bed on the opposite side of Vicki. Rob is lying on the bed between us and of course we're lined up with his cock, as I'm sure that's what Vicki intended.

"So you've never even gotten a blow job before?" Vicki asks me.

I simply respond "No."

"I bet you never imagined you'd be giving a blow job before you ever got one." She says with a laugh. And when she says that, Rob takes the pillow that he was previously lying his head on and instead moves it to on top of his face, as if to shield him from what's about to happen.

"Why don't you start by putting it in your mouth. Maybe that'll finally be the thing that gets him hard." Vicki tells me.

I feel sick to my stomach, extremely nervous, and yet slightly aroused all at once. It's by far the most uncomfortable I've felt so far during this whole ordeal. While I had experimented plenty of times with things in my ass before, I had never once contemplated giving a guy head. Nonetheless, I lift my self up and position my head above Rob's soft and uncircumcised penis and I use my hands to try and push down his foreskin to reveal his shaft and head. He has a fair amount of pubic hair, more than I do, so it's kind of forming a bush all around that I have to keep down. I'm able to expose his tip a little, but it's still pretty far from a normal erection, so there's not much there. But I use both my hands to push everything down and force up his soft penis, and then I lean over and easily take the whole thing into my mouth.

"Perrrrrfect." Vicki says in approval. While Rob's penis is in my mouth, I'm not doing much with it other than just keeping it there. It actually doesn't taste like much. It tastes a little like sweat and body odor, but nothing too strong. It's weird as fuck, but the only thing that's going through my mind is how the hell is Rob not getting hard? Is it just because he's so used to getting blow jobs from girls that he doesn't even have the slightest involuntary reaction to this?

"Ok, suck on it. Like I want to hear you sucking it." Vicki now tells me.

So I do. I basically suck on it like a lollipop and use my hands to try keep everything else out of the way. As I do this, I can tell it is growing, but only slightly. As it gets bigger it becomes easier and easier to suck. I can't believe I'm actually sucking a cock right now, but I'm so caught up in just following Vicki's instructions that I don't even worry about the big picture of what I'm doing.

Now while I keep sucking, eventually it seems like any progress I made in getting Rob hard starts to fade as he goes back to being pretty limp and soft. Eventually, Vicki sees this.

"Ok, hold on. Take a break for a sec." She tells me. "This just still isn't working." She says with a disappointed tone, and then she looks at me and says, "It's not you, it's him. You're doing great."

Next thing I know, Vicki stands up off of the floor and does something totally unexpected. She unbuttons her jeans and slides them and her panties immediately off with no warning. For the first time in my life, I am seeing a naked vagina in person. This is definitely the best silver lining yet of this whole experience.