Poster Boy Pt. 03: 2 Sides to Every "Hole"

"I swear I didn't know you were Tony's roommate though!"

"So...you spied on me changing clothes or something, and took pictures of me naked!? When did this happen? Who's going to see them?!" He's starting to freak out a bit.

"Well basically, yeah." I feel horrible. "I swear, I cropped your face out though! There is no way anyone could tell it's you. It happened earlier this week after your yoga class."

"After yoga?" I can see him thinking back to that day and his eyes widen a bit as he remembers masturbating when he got home.

He looks at me, his face flush with embarrassment, "Did you...did you watch me jerk off? Did you take pictures of that?"

I hang my head in shame and come clean. "Ahhh, well...yeah." There is a long awkward silence while he processes everything.

I speak first, "I'm so sorry! I really wanted to tell you everything after we left the movies the other day, but I couldn't figure out what to say."

He just stares at me, gauging my sincerity, I guess.

"Is there anything I can do or say to make things right between us?" I offer. I knew in my heart I should have told him about this right away but I chickened out. Now I fucked everything up! I can feel the tears welling up in my eyes.

After a long pause, he finally says, "Do you mean it? Will you really do anything to make it up to me?"

"Yes!" I say happily. "Whatever you want. Whatever I can do!"

Ken hugs me, wrapping his strong arms around me stroking my hair and back. I lift my head and he leans over and kisses me softly.

"Did you like watching me masturbate? Did it turn you on?" He asks.

I chuckle and blush, "Yeah it did. It was very hot! It made me so horny I touched myself!"

He kisses me again, harder this time. His hands move down my body and he grabs my ass cheeks and firmly squeezes them.

Breaking our kiss he looks into my eyes, "Did you finger your pussy? Did you make yourself cum?"

"I did. I rubbed my hot little pussy watching you stroke your beautiful dick. Then when you lay face down on your bed with your sexy ass pumping your dick beneath you, it looked so hot I came really hard!" I'm hoping my sexy description will help him forgive me.

"Well I think there is only one fair solution to this matter, don't you?"

I look at him puzzled. I'm not really sure what it is he's thinking of, but I'll do whatever I can to put this behind us.

"Take off your clothes and let me watch you masturbate," He tells me.

I burst out laughing, "You're joking!" He's smiling but I can tell he's not joking.

"If you honestly want to make it up to me; since you watched me masturbate, I should get a chance to watch you. Fair is fair, after all. Hey, at least you have a choice, I didn't!" he tells me.

As an adult I've never even been fully naked in front of another person, let alone masturbated in front of someone. Even though we had sex that one time, I wasn't actually naked and it was dark. I don't know why I'm hesitating though, because I came over today expecting and hoping to have sex with him again and he is going to see me naked eventually anyway.

I feel a tingle in my vagina as the idea of exposing and pleasuring myself for him settles into my mind. I think back to how I felt as I watched him stroke his cock, and I before I even realize that I've decided to do it, my hands are unbuttoning my blouse.

Seeing that I've settled on granting his request, Ken pulls his desk chair to the foot of the bed just to the left of the poster, then walks over to the dresser and removers a brand new tube of lube and a condom from one of the drawers. Finding what he needs he returns to the chair, and takes a seat in anticipation of the show I'm about to put on.

As I undress my eyes shift to the postered wall just behind him. From this angle I can make out the faint trace of something just below the poster, that has splattered on the wall and dripped down, then dried.

Oh my God! Not only did he watch them having sex, he jerked off to them!

My clit spams with arousal at the thought of his voyeurism. I glance back to the hole in the poster. Its funny once you know it's there it's so obvious.

What if someone is looking through it right now?

No. No one else is here. Besides, I looked through the hole and the other poster is up. Still the idea of someone possibly watching me is making my nipples hard. I can feel them pushing forward against the fabric of my bra.

But what if this is part of his plan for me to experience what he went through?

That's impossible because he just found out what I did.

Unless Barb told Tony and he told Ken.

Ann get a hold of yourself, this isn't a conspiracy! Unless...am I actually hoping someone is spying on me?

I think back to making love in the theater and I remember the faintly lit faces of the other movie goers staring back at me as Ken pounded me with his dick. The thought that they were watching me getting fucked and it was turning them on, really excited me.

I'm sure Ken didn't realize it at the time, but when he had his hands on my hips fucking me from behind, I pulled up my blouse up high enough so that the audience could see my bouncing tits. I came shortly after that as I stared at the lustful looks of all those strangers!

I'm undressed now except for my underwear.

I pause to look at him for a second before removing my matching lavender bra and panty set in case he has decided to take pity on me and give me a reprieve.

Nope, no such luck.

Secretly I'm glad he isn't stopping me at this point, because the closer I get to being naked, the hornier I'm becoming. Turning around I reach behind me and unsnap my bra and remove it without hesitation. I'm so aroused now that my panties are pretty wet. Sliding them off I glance at the crotch and see that it's coated with pre-cum. I quickly bunch them up and put them off to the side.

Now fully naked, I spin back to face him, giving him a good view of all my naked glory. I notice his left hand is rubbing the crotch of his jeans and a nice sized lump has developed there.

"Sit back on the bed. That side, where I was," he points to where he sat when I spied on him.

Leaning my back against the wall like he did, I spread my legs and pull the lips of my pussy apart giving him a nice view of my clit and glistening wet hole. Now that I've committed to masturbating for him the idea of it has me very turned on. Glancing up at him I see he has undone his jeans and his hand is groping his cock inside his underwear.

"Yeah sweetheart, that looks so sexy!" he says, his voice trembling slightly with excitement. "Rub your clit for me baby."

Using light circular strokes, I run the tips of my right fore and middle fingers around my clit. The sound of my breathing has become noticeable in the quiet of the room.

I'm staring at the hole in the poster for a good ten seconds before I'm even aware that my eyes have gone there. My rational mind knows no one is looking, but knowing that hole is there gives me the feeling that I'm being watched by some unknown person. It's like when you look at the eyes of a painted portrait and it feels as if they are following you around the room.

Real or imagined, the thought of a stranger spying on me is thrilling and adds to my excitement, sending a ripple of pleasure cascading across my body, making it jerk.

I return my attention back to Ken since he is actually here and observing me quite intently. It's my turn to watch him now as he releases his long hard cock from his underwear and applies some lube to it. He looks so sexy stroking his glistening dick.

"Turnover and show me your ass." He commands me.

I like that he has taken control and is instructing me what to do and how to position myself, because it allows me to be "slutty" without it being my fault. I turn face down on the bed, then raise my ass up as high as I can while still being on my knees. I point my butt it in his direction and wiggle it a little.

"Like this, hon?" I say trying my best to sound naive.

The side of my face and my tits are lying on the mattress allowing me to spread my thighs and reach back between them to rub my dripping wet pussy. I can feel my asshole relax enough in this position to gape slightly. A bit of cool air fills my open rectum. I angle my head and upper body to the side just enough to watch him jerk off as he watches me masturbate.

"Fuck that's so hot! I love your beautiful sexy ass, Ann!" he says complimenting me.

I see that while I was switching positions he had enough time to remove his pants and underwear. He's pumping his long hard cock quicker now, obviously very excited by the view of my naked butt. I'm totally caught off guard though, when Ken lift his phone up to my butt and take a few pictures.

"Hey, what are you doing!" I bark. I sound outraged but in my heart know I can't really complain and I'd never admit it but knowing that my ass and pussy are on display for his picture taking delight is actually making me even wetter than I was.

"Fair is fair babe!" He grins devilishly.

Feeling that we are now even, Ken places his phone on the chest of drawers and walks over to the side of the bed, and drops a condom and the lube next to me. He continues to jack is cock with his left hand, and runs his right hand all around my ass. When his fingers finally settle onto my pussy I can't help but moan and push back against his hand.

His fingers slowly work there way around my pussy taking their time to explore and caress every part of me. It feels amazing when he slips one, then a second finger into me, wiggling them around. I love the sound of his fingers churning around in my sloppy pussy; it's so raunchy and sexy!

Fuck! I'm so horny I really want his hard cock inside me!

I'm more than a bit surprised when he removes his hand from my vagina and slides the tip of his moisten finger into my asshole. Ever so slowly he slides into me further and further until the entire length of his finger is up my ass. I moan a bit louder at this new sensation.

When I masturbate, which honestly I don't do that often, I never play with my ass. It's never even occurred to me that this is something that could be pleasurable. Then again sex, in all it's forms, nuances and possibilities is new to me, so I guess I shouldn't be so shocked. I know I have a lot to learn.

I do my best to relax and just enjoy what he's doing to me, trusting that he would never do anything to hurt me, and trying not to think about if this is right or wrong. I have no doubt if he did do something that I really didn't like, he would stop if I asked him to.

Since he's gone from observer to participant, I push my upper body off the bed so that I'm on all fours and take the tip of his cock between my lips. It's flavored with the slightly sweet yet acrid taste of lube and pre-cum but I'm to horny to care. I slide the length of his slick dick as far into my mouth as I can. Ken places his free hand on the back of my head as I blow him and continues to finger fuck my ass with his other.

Off in the distance I can hear the apartment door open and close and the muffled sound of talking. It has it be Tony and a guest. Seconds later his deep voice is at Ken's bedroom door.

"Ken? I'm home with Barb."

"Alright, I have company as well!" Ken responds turning his head towards the door. It isn't locked so thankfully Tony is respectfully enough not to open it.

It's amazing how easily sound travels through the thin door.

I can clearly hear Tony tell Barb, "Babe why don't you make yourself at home. I need to use the "can" and then I'm going to take a quick shower."

Barb's voice is unmistakable, "Sure hon. Take your time," I hear her enter Tony's bedroom and close the door behind her.

It's weird to hear my girlfriends voice when I have a cock in my mouth and a finger up my ass, but Ken seems unfazed by the fact that there are two other people in the apartment. Judging from how hard he is I'd say he's probably just too horny to care.

I completely understand because I don't even think of stopping what I'm doing. I'm thrilled when he says, "Turn this way Ann, I need to fuck you!"

Ken doesn't join me but opts to stay standing at the side of the bed. He opens the condom packet then rolls the 'rubber' down the top two thirds of his beautiful erection.

It dawns on me as I turn my ass towards his dick that if I can easily hear Barb, she can just as easily hear us.

Did she just hear Ken say he needs to fuck me?

Instead of feeling embarrassed like I would normally expect to under these circumstances, I feel my clit pulsate with the thrill of being caught having sex, and I involuntary picture her watching Ken fuck me.

He wastes no time and slips his thick hard-on easily into my soaked pussy. I can't help but let out a moan loud enough that I have no doubt Barb can hear.

Oh my God! This feels sooooo fucking good!

Ken must know that sound travels here but he doesn't seem to be making any effort to be quiet either.

On the contrary he says rather loudly, "Ann your pussy is so fucking hot! Fuck me baby! Give me that pussy!"

He's fucking me hard; his hands are on my hips and I think it's his thumb I feel probing my asshole. I have to say I'm finding the added stimulation of having my ass fingered a real turn on. I can feel an orgasm building quickly.

"Do you like my finger in your asshole Ann?" Ken grunts and pants. "God your ass is so fucking hot and sexy! Can I stick my dick in your ass sweetheart! Please! Can I fuck you in the ass?!"

Oh shit! A finger is one thing but his dick is so much bigger!

His finger feels great but I'm scared it will hurt if he sticks his cock in my tight virgin asshole.

"Ummmm...I don't know babe." Even as I say it I know I'll try it he asks me again.

"Please hon, I'll go slow. I promise," he assures me.

"Okay, but if I say stop you have to stop."

"Of course!"

He picks up the tube of lube and squirts a generous glob of it onto my asshole then works it in with a finger. His cock is still in my pussy, slowly sliding in and out of me. I try my best to relax my rectum as he gently and slowly enters me with a second finger. Truthfully I'm surprised that he is able to work two fingers in me without too much discomfort. As I pant from the sensation of his probing fingers, I realize breathing is a very important tool to help me relax.

Breath, I have to breath.

Off in the distance I hear the toilet flush. I guess Tony has finished pooping. For a second an image passes by my brain of me squeezing my anus and pooping out Ken's fingers, making me giggle.

Thinking of Tony makes me remember that Barb is in his room and can hear just about every sound we make. I wonder if she would be tempted to spy on us as well. I glance at the hole in the poster. Is it my imagination or do I see a glimpse of light and movement?

A wave of lust washes over me at the thought of her spying on me.

"Now baby, fuck my ass, sweetheart!" I moan.

I don't have to tell him twice. He slides his cock out of my pussy and presses it against my stretched and ready asshole. I feel the pressure of his dick head forcing its way into my tiny tight hole and a pinch of pain.

"Wait!" I moan loudly.

Ken stops instantly waiting for permission to carry on.

I'm panting as a tear drips out of the corner of my eye and rolls onto the bed.

Relax. Relax and breath.

Then pain subsides and despite the initial discomfort there is something exciting, erotic and pleasurable about this and it makes me want to continue.

"Okay, I'm ready. Try again." I tell him.

He slowly works is cock in a little more. Once he has the first inch or so in me, the rest follows with surprising ease. I let out a long, loud moan as he inches the full length of his dick all the way up my ass.

I concentrate on this new sensation of anal sex and let the pleasure of it over take me. It's an unusual combination pain, pressure and pleasure and ok there is a bit of that familiar feeling like I really need to poop, but beyond that it's mostly just intense pleasure radiating out from the center of my being! I rub my pussy and clit and notice that the sensitivity in those nerve endings is dialed up to eleven (shit more like 15!)

From the other room I can hear Tony turn on the shower and I know it won't be long before he finishes and joins Barb in the bedroom. I really want to cum before that happens and I'm so horny I don't think it should be a problem.

My eyes have been on the poster this whole time. I look again at the dried cum stains just below it and think how apropos this situation is. I spied on Ken, he spied on Barb, and now she is spying on us! I think of Ken telling me earlier, 'Fair is fair', and he's right. I picture Barb on the other side of the wall with her hand in her panties stroking her clit, just like I did when I spied on Ken masturbating.

My orgasm is building and I'm getting really close. Ken is grunting and fucking my asshole all out, so I can tell he is seconds away from cumming as well.

"Rub that pussy baby! Rub it hard!" I'm actually talking to Barb but naturally Ken thinks I'm speaking to him. He slides his hand from my hip, around to my pussy. I move my hand out of the way and he takes over grinding my super sensitive clit back and forth. Since my right hand is now free I use it to pinch my nipples. I'm on all fours now pushing back against his dick as hard as I can as well.

"Fuuuuuck! Fuck me hard and make me cum!" I groan loudly.

It's not easy to tell over the moans, grunts and loud sounds of sex in the room but I think I can hear moaning coming from behind the poster as well.

Then I'm over the edge! Oh my God, sweet release! I'm cumming so hard my upper body collapses onto the bed even though my ass is still being pummeled by Ken's crazy hard cock! My asshole spasms and quivers squeezing his dick even more than it already was. I lose all motor control of my body, and all that matters at this moment is riding wave after wave of immeasurably intense bliss! I never knew my body could feel anything this incredible!

I'm still in the midst of my orgasm when Ken moans, "I'm cumming baby!"

He continues to slam his dick in my ass unloading his spunk deep within me. It could just be my imagination because I know Ken is actually coming into the condom, but I seem to feel the heat of his cum radiating out from deep inside my ass.

Ken finally finishes and collapses next to me on the bed. Our heavy panting slowly settles and I hear Tony exiting the bathroom, his shower completed. A few steps later his bedroom door opens and closes.

The wall between us does nothing to mask the surprise and lust in his deep voice as I hear him say, "Wow, baby! I see you started without me!" Barb giggles, and the sound of the bed groaning under the additional weight of Tony's large frame passes through the porous wall. "Damn! The fucking poster fell off the wall again! I really need to get maintenance to fix that hole!" Tony sounds more than a little annoyed.

"Shhh, forget about that hon." Barb says, "l have a hole that needs fixing for you, right here! Now give me that big dick!"

Hummm...I wonder if Ken would mind if I take a peek! Hahahaha!