A "hole" New Story

Author's note - the following is the first of a three part series. The second part "Poster boy - fun at the movies" (will be under 'erotic couplings' section) continues the exploits of Ann and Ken, and "Poster boy - 2 sides to every hole" finishes the series.

My friend Ann asked me to write this for her. Ann and Ken are based on real people but the situation is fictitious. I hope you will give all three parts a try.

Thank you and enjoy! :)

*****

Ann chapter 1

"Come on Ann, today's the last day and you don't have any points! We promised each other that we would pledge 'Alpha Sigma Sigma' together! Lisa's covered her points, and I have mine. Today's the deadline! You have to send your pictures in by 8:00 pm!" Barb pleads.

Crap! It's too early in the morning to deal with this shit, and we have five minutes to get to our first class of the day. "I know, I know! I'm trying! It's not easy! I'm not sure what I can do!" I bark, annoyed that they keep hounding me about this.

It's very frustrating because I really don't want to let the girls down, but I'm running out of time and I'm at a loss as to how to get the points I need. Why do sororities have to give us these stupid challenges in order to pledge anyway! We had a number of different tasks to complete over this past week and I had no problem with the other requirements.

It's just this last test; to take and send in pictures of guy's butts and penises that has me stumped. Barb had it easy. She has a boyfriend and he texts her pictures of his hard-on all the time. Boom! 100 points and she was done.

Lisa's friend, Tina, helped her out so she kind of cheated, actually. Tina lives at home and has three brothers, all sharing one bathroom, so she sees them naked all the time. She had no problem sneakily using Lisa's phone to snap two butt shots (25 points each) and one penis shot (50 points) for her 100 points.

I, on the other hand don't have a boyfriend; have four sisters, and don't have a friend that can do it for me, so I'm stuck.

"That's okay, I have a plan!" Barb says with pride. "You're so freaking lucky to have me as a friend!" she laughs. "Remember that party at the end of the last semester when Tony got drunk and some guy bet him he couldn't punch through his dorm room wall? Well, I'm over at Tony's place all the time and I know they haven't repaired that hole yet. Typical men, they don't care. They just stuck a poster over it and called it done. So if you were to poke a hole in his roommates poster you could spy into his bedroom!"

"Wait, you want me to spy on your boyfriend's roommate?" I say with surprised disbelief.

"Do you have a better idea?" Lisa chimes in.

I've racked my brain for days now and couldn't come up with anything. "No, I guess I don't," I say defeated. "But how would I get in there; what about Tony? I can't just randomly wait around to see his roommate naked!"

"I have it all figured out!" Barb says, very happy with herself. "Today at 11:30 I'm going over to Tony's dorm room so we can have sex while his roommate is in class. Tony has class at 1:00 so he'll leave the apartment around 12:50. When we're done I'll take my time getting dressed and stay behind.

"Ann, make sure you are waiting down the hall, and after he leaves I'll let you in. Tony's roommate usually comes back a little after 1 from his PE class and takes a shower. All you have to do is spy on him through a hole in the poster and wait for him to undress, then take a picture and leave. It couldn't be easier!

"Hopefully you get a 50 point penis shot, then we'll figure out something else for the other 50 points. There's gotta be a couple of guys that we can convince to moon us, or something. Anyway we'll deal with that later."

Barb's always optimistic. It's one of her strongest points, and it can be very contagious. She makes it sound so easy and totally feasible.

"Oh my God, I can't believe I'm going to do this," I say full of doubt but resigned to the fact that I have to try.

...

I wait anxiously in the hall just down from Tony's dorm room, and just as Barb said, around ten to one Tony steps out and hurries off to class. A few seconds later Barb sticks her head out looking for me and we hustle through the apartment door nervously giggling.

All the rooms in this dormitory look the same so I know the simple layout already. The door of the apartment opens on to the kitchen/dining/living room combination. On the far side of the room, just off the kitchen area are two doors side by side that lead to the two bedrooms. A short hallway is formed by that wall and the end of the kitchen, which leads to the bathroom.

The only real question is which one is Tony's room. Barb takes the lead and escorts me through the door on the right. The bed is a mess and the scent of sex still hangs in the stagnate air. Barb has already removed a beautiful poster of some sun drenched lush rolling hills with the word "Tuscany" emblazoned atop, and placed it on the disheveled heap of bedding.

The hole on this side of the damaged wall is much larger than I expected, and I can easily place my whole face in it. I don't have far to go because the smaller fist sized hole on the opposing side, is only three inches away.

"Okay we have to hurry, he's going to be here any minute! I already made a hole in the other poster..." Barb says pointing to a pencil width size hole in the piece of paper hanging on the roommates side of the wall. "but you can't see as much of his room as I was hoping."

I put my eye up to the spy hole and peak in. All I can see is most of his dresser and about two thirds of his neatly made bed. Unless he stands naked in front of his dresser, or lays naked on his bed, I won't be able to get the shot I need.

"Barb I can barely see anything!"

"Sorry! I can't make the hole any bigger or he'll see it! Hopefully he'll strip off his clothes and walk naked over to the dresser to get some clean clothes or underwear, then you can get the shot you need!" Barb's desperate optimism is getting old.

"I don't know, that seems like a stretch." A horrifying thought suddenly dawns on me, "Wait...how the hell do I get out of here without him seeing me!"

Barb stares at me blankly for a second and I realize she didn't think this far ahead. "Well, I guess you take the picture, put the poster back on the wall (

DO NOT

forget to do that!), and listen for him to go take shower, and leave."

"Yeah but what if he

doesn't shower

?" I say, a little panicked. "Then I could be stuck in here until Tony gets back!"

I can clearly see Barb's mind scrambling for ideas to put me at ease. "Well you'll just have to sneak out before he's fully dressed; while he's still in his room, I guess. I don't know, you'll have to figure it out!"

A pang of dread strikes me in my heart like a spike. "Shit! This isn't going to work! We gotta get out of here!"

"Come on Ann, you can do this! I gotta go, he's going to be here any minute!" Barb grabs my arm her eyes begging me to stay and get the job done.

Full of fear and doubt, but armed with the knowledge that to leave means failure and disappointing her and Lisa, I reluctantly say, "Fine, I'll try."

Barb smiles, says good luck, and rushes out.

...

Ken chapter 1

I was really disappointed at first that the bowling PE elective was filled forcing me to take yoga, but I have to say, I'm enjoying it much more than I thought I would. It's been great to stretch and strengthen my muscles, and afterwards I feel really relaxed and amazingly re-energized.

I head down the hall towards my dorm as Barb, Tony's girlfriend, rushes past me. We exchange passing "Hi"'s, but I catch a glimpse of a weird smile on her face like someone who got busted with her hand in the cookie jar.

Could she be embarrassed that I caught her sneaking off after she and Tony just had sex? That's odd because It's not exactly a secret. I know that they have sex when I'm in class and I obviously don't care. She also sleeps over every couple of nights and I hear them having sex all the time. Perhaps I misread her expression.

I enter the apartment and head past the kitchen to my room.

Pausing outside of my roomy's door I say, "Tony? You home?"

No response. He should be in class by now but it doesn't hurt to double check. It's always more relaxing to have the place all to myself and I prefer the additional privacy if I decide to masturbate (hehe, which I probably will).

I head into my room and walk over to my closet. Sitting on the bed I remove my sneakers and socks and toss them in the corner in front of my clothes hamper. My yoga clothes are damp with sweat and I peel them off and throw them basketball style into the narrow free standing hamper.

He shoots, he scores!

Standing naked in front of the closet mirror I flex my muscles and admire myself. Employing a few standard bodybuilder poses I twist side to side a little so I can view my muscles from every angle.

I'm lean and have no resemblance at all to a body builder, but for someone who was always very skinny as a kid, it's encouraging to me that I've put on about twenty pounds of muscle over the past year and I finally feel like I'm rounding into an attractive adult. It's really helped me gain confidence and combat my shyness and insecurities.

I like that my shoulders are broad and my biceps finally have some definition and a nice peak when I flex them. Thankfully even though I'm slim, I'm a little over six feet tall so I also have that going for me. I definitely look much more athletic now and not as dorky as I did a year ago.

Hey, not to bad.

You sexy devil!

I joke to myself.

I shift my focus and admire my dick for a second. The other good thing about yoga is that the class is primarily made up of hot girls! I grab my cock and give it a squeeze as I think about all those sexy asses in the "downward dog" position. My cock twitches in my hand.

Damn I'm horny! I really need to get a girlfriend, and soon! In the meantime thank God for free porn!

I take my iPad and a box of tissues off my desk and toss them onto the bed. Walking across the room to the dresser, I slide the second draw open and reach for my jar of Vaseline, then sit on my bed with my back against the cool wall.

I switch on the iPad and place a couple of tissues under my semi hard cock to catch any cum that may drip down. I find sitting with my feet together, knees bent exposing my crotch, with the iPad on my right thigh, to be the most comfortable and convenient position to masturbate in while watching porn.

Thanks to my yoga class I now know this is called the "butterfly" pose

, I laugh to myself.

I dig a glob of Vaseline out of the container with my left forefinger and apply it to my dick. Balancing the iPad on my right thigh I type in my favorite porn site and surf through various video options looking for something to make me hard.

Here we go, "lesbian massage seduction." Damn I love porn!

There is nothing I enjoy more than watching horny naked women. I love everything about a woman's body, from the soft sweeping curves of their breasts and asses, to their beautiful faces. The only thing that's sexier than a naked woman is two naked women together!

I select a video of a straight girl receiving, what she thinks is a free massage by a sexy professional female masseuse, only to get seduced into unexpected first time lesbian sex. It doesn't take long for my cock to get fully hard. I vary the speed of my strokes to bring myself to the brink of an orgasm then slow my pace to prolong my pleasure. I switch to another video and continue to masturbate.

Fuck, I wish I knew what it felt like to have my hard cock in a woman's hot wet pussy. I can't believe I'm almost 23 and I still haven't had sex yet!

I was way too shy and insecure in high school to date and I took a couple of years off after my freshman year at university to work for my dad, which really put a damper on my social life. Truth be told, I finally decided to enroll again in college because I knew it was the best place to meet girls my age and that if I didn't return to school now I probably never would.

The female population of this school stands at lofty 75%, and while there were other considerations that were important to me in selecting a school, without a doubt that was at the top of my list! With three girls to every guy I have to believe that it's only a matter of time before I meet one of them and get lucky.

I already have my eye on this girl Ann, from my art history class. She happened to be sitting next to me that first day of class and we chatted for a while at the end of it. Art history convenes twice a week, and after that second meeting we spoke again as I walked her to her next class. I definitely plan to ask her out the next time I see her.

She's so pretty and very sweet with a great sense of humor. I love how fit she is, with nicely shaped breasts and a tiny waist that transitions into curvaceous hips and a very sexy ass. I really hope she doesn't have a boyfriend already, cause that would suck!

As I pound my cock I think of her pretty face hiding behind her black plastic rimmed glasses (what can I say, I think the slightly "nerdy" look is kind of hot, actually). She smiles, encouraging me to explore everything she has to offer and I let my horny mind wander across her naked body.

Fuck! Thinking of her is making hornier than this stupid video.

I pause for a second on the edge of an orgasm and my cock pulsates in protest, demanding that I continue to stroke it. I toss the iPad to the side and I stand up to reposition myself on the bed. I lie face down with both hands together beneath me forming a tube. Sliding my diamond hard dick into my finger simulated pussy, I slowly pump my ass up and down pretending it's Ann's tight hole squeezing my desperate dick.

God I'm so fucking horny! I hope her real pussy feels this fucking good!

I visualize Ann naked and sucking eagerly on my thick cock as I fuck my "hand pussy". With each passing second I thrust a little harder; my ass rising and falling with enough effort now to make the bed bounce. Increasing my tempo faster and faster my only goal at this point is to release the tension in my balls.

My fantasy scene morphs into me squeezing and sucking on Ann's sexy tits and kissing her luscious mouth.

I'm not sure if it's just my imagination or not, but it definitely feels different to slide my cock in and out of my stationary hands as if I'm fucking someone, than it does to side my hand up and down my stationary cock. Perhaps it's because the motion is more like real sex and it tricks my mind easier, but whatever the reason, It feels fucking awesome!

I visualize my dick sliding into Ann's sexy little asshole now and I'm fucking my hand so hard that the "thump" "thump" "thumping" on the bed is making it creak loudly.

Oh shit! This is so fucking good I'm going to cum!

My balls finally spit their load, and as I orgasm I think of my cock slamming into Ann's tight wet pussy.

"Oh fuck!" I grunt. "Fuck me Ann! Give me that beautiful fucking pussy!" I mutter out loud as I cum.

Hot sticky jism floods my fingers and wets my quilt. I continue to stroke my dick for a bit after my orgasm, laying there for a while catching my breath and squishing my stiff dick around in my spunk.

I'm still hard when I roll over and use the tissues to wipe the sticky load off my penis, but my erection fades fast once I get up and take a few minutes to clean off my bed, throw out the used tissues and put away my iPad and Vaseline. Grabbing some clean clothes and underwear from my dresser, I wrap a towel around me and finally head to the bathroom to shower.

Passing Tony's door I notice it's slightly ajar.

Hummm, that's strange because I'm certain it was pulled shut when I came home.

"Tony?" I say, not really expecting a response but just checking to be sure. I push his door open and scan his messy room. Just as I suspected no one is there. The top left corner of the poster he put up to cover the giant hole he punched in the wall has peeled away though; folded down forming a white triangle covering the front half of the title word. Only the letters "cany" are visible but out of the corner of my eye, I mistakenly read it as "cuny".

Hehe! Talk about a Freudian slip! I definitely have a one track mind. We really need to get maintenance to patch this stupid hole, though.

Turning to leave, I pick up a musky scent that I instinctively know is wet vagina, intermixed with a subtle floral perfumy smell lingering in the air. I would have to say my sense of smell is by far my least developed sense, and yet this unmistakable scent of a woman literally causes my penis to twitch with the expectation of sex.

Damn! I really need to get laid!

I lift the loose corner of the poster back to the wall and firmly press on the tape, then pull the door closed behind me.

...

Ann chapter 2

I don't have long to wait before I hear someone enter the apartment and walk towards me.

"Tony? You home?" a voice says outside the bedroom door.

I hold my breath and pray he doesn't open the door. My heart is beating so hard with the fear of being caught that my breathing is shallow and quick and I feel slightly light headed. After a small pause, the other bedroom door opens and a blur of movement passes in front of the tiny spy hole.

Out of my view the bed moves under the weight of someone's body then I hear the thump...thump, of their shoes hitting the floor. I can't see the person undress because he's too far over and out of my line of sight, but I hear some rustling like someone removing their clothes followed by the sound of them being thrown and landing on the floor or maybe in a hamper.

Well hopefully he's naked at least. Come on dude, walk over here and let's get this over with!

Each second I wait for him to walk in front of the spy hole seems like minutes; minutes like an eternity.

What the hell is he doing?

I'm starting to think he's never going to walk into my viewing angle at all, when surprisingly I see an iPad and a box of tissues hit the bed.

Come on dude, just walk to the dresser and let me take a picture so I can get out of here.

I position the camera lens of my phone in front of the spy hole and wait. Seconds later the round white bum of a tall slim man with broad shoulders comes into view and I snap a shot.

Cute ass!

He stops at the dresser and opens the second drawer from the top and pulls out a jar or small container but no clothing. I get a glimpse of his dick but he turns towards the bed too quickly for me to snap a picture. I have no choice but to wait and see if I get another opportunity.

Moving from the dresser he sits on the bed and leans his back against the wall folding his legs in some kind of an Indian style position. His legs are spread exposing is crotch so I have a clear shot of his penis. I have to admit it's not everyday I see a naked man and my nervous adrenaline now mixes with a rush of arousal.

I take another picture then lower the phone. Putting my eye back to the spy hole I try and get a better look of the guy and his dick. Staring closer, my jaw literally drops as the guy's face comes into focus.

Holy shit that's Ken from art history!

I'm even more shocked as I watch him scoop something on his fingertip from that jar and work it onto his dick.

Oh fuck! He's going to masturbate!

I know I should leave right now, even though a picture of an erection gets me all the points I need, but my eye is glued to the spy hole. I feel horrible because he seems like a really nice guy and I like him. Plus he's cute and as I can now see, even sexier than I first realised!