Tales of a Virgin

She flashes a nervous smile as she slides her lacy blue boy shorts down past her knees and off her feet. She has olive skin, bright green eyes and dark brown hair. Her tan little upturned nose has been kissed by the sun and is covered in tiny brown polka dots. I lean in and give it a peck with my lips, she grins and eases herself on to my bed trying to prevent the wretched squeak that the old springs produce.

We are both 18 and spending our senior year working our way through the awkwardness of sexual learning.  See, up until last week, we were both still virgins¹ with the exception of her occasionally letting me fuck her in the butt. I am not quite sure why that was acceptable but she always told me, “you can’t get my butt pregnant!” For being such a lovely young lady I always wondered where she acquired that very redneck quip. I’d shrug off the comment, lube up my main vein and go diving in.

¹Read chapter: I “accidentally” missed her b-hole and wedged my penis in to her vagina and then she cried for an hour about no longer being a virgin.²

²It’s a working title.

Truth be told, I am just happy she still let’s me stick it in her number two slot. Considering the first time I did plow in to her asshole, we were unaware that she should take a shit BEFORE we had sex. She screamed, I pulled out then turned on the light. The poor girl had shit all over me and my bed. “This could have gone better.” I thought as we sat naked in the excrement and I embraced her with a shitty hug as she wept in to my pathetic boney chest.

My first sexual experiences were obviously not romantic in any sense of the word and not one of them lasted more than two minutes. This time of my life is actually when I discover that girls grow hair around their buttholes too. “Gross!” I thought, looking at her ass cheeks spread apart kneeling down in the doggy position as she looked over her shoulder smiling at me, “It looks like a squashed spider.” And it truly did! It was a dark circle with crooked spider-leg-looking pubes straying in all different directions. I wince now just thinking about it, but none the less she was beautiful, and most importantly, she was mine. A couple of wiry butthole pubes weren’t going to stop this guy!

Too say this girl is out of my league would be an understatement. She’s smart, attractive, the captain of the volleyball team and the homecoming queen. Me on the other hand, I stand all of 5’7” tall weighing 130 pounds soaking wet. Between my Chuck Taylors that are a size too big, my wannabe grunge rocker flannel shirt, ripped jeans and shaggy hair, I make for a terrible athlete. “Way to go boys!” I squeal from the sidelines like a total homo. “My hands are looking exceptionally tough today.” I note while looking at my newly formed calluses from the excessive clapping. I think of myself as a good athlete that doesn’t get enough playing time to show his true potential, but as I get older I will face reality, I was fucking terrible.

I remember back to my junior year when I was once forced to write a hand written apology to our whole football team, followed by doing 100 burpees. All this for screaming “Touchdown!” as a far better team scored its 50^th point against us in a single game. So not only did I suck, but apparently I was a traitor too. “I said I’m sorry!” I gasped to my coach while vomiting through my one hundredth burpee. “Not sorry enough.” He said like a prick, and then instructed me to run laps until practice was over or I died. He was a true inspiration. Fortunately for me I got the last laugh; he was fired after getting caught watching porn on his laptop in the boy’s bathroom. “Hey coach!” I yelled as I held the gymnasium door open watching him cross the parking lot with all his belongings, “Suck a dick!” I slammed the door running inside the gym giggling like a girl, so proud of my accomplishment. 

But that’s enough reminiscing of my pathetic sports career; let’s take our focus back to the naked girl in my bed shall we?

So here she is, my first love, sitting on my bed waiting to accept me. Her breasts are extremely large and coursed with veins similar to that of my grandmother’s legs. That reference grosses me out, but the tit’s themselves, to me they’re perfect. She has a thin waist and her tight ass that looks great in a pair of blue jeans. Her thin waist gives way to a large patch of razor burn where her “I’m still a virgin” bush used to be. I snicker at the red bumps then glance down to see that my razor burn is twice as bad where my “I’m still a virgin” bush used to be. I turn my focus back to her, as she blushes and covers her vagina with her hands. Her knobby knees are pushed together as she anxiously plays footsie with herself.

I lay her down on to her back as I crawl on top listening to my lousy day bed let out a series of squeaks and yelps. “Shit” I mutter, “we have to be quiet!” See, my bedroom is connected to the living room and my bed sits right in front of my bedroom door. My mom and dad are currently in the living room staring at our cordless phone, waiting for a ring. My cousin Bret was in a car wreck tonight and his condition grows worse by the hour. I love my cousin Bret, but he’s three hours away and there is nothing I can do for him now.

For a moment I pause while sprawled out naked across my first love and think back to my cousin. See, Bret was always my idle growing up. He was almost a decade older than me and grew up doing all the hillbilly things I wanted to do, he was crazy. Motorcross was his favorite sport and he’d always ride wheelies up and down the dirt road in front of his house. He was a four year letter winner in football and won state in wrestling. His free time was spent hunting, fishing and working on his 1969 Camaro he had purchased from an old farmer after he spent a whole summer working in that same old man’s fields.  Bret was everything I wanted to be, but as we grew older, his coolness faded. He went from being the awesome cousin that taught me everything, to another white-trash kid hooked on crank (which is like meth’s redneck cousin according to Dave Attell.)

Bret and I have since grown apart and years have passed without us talking. Plus, I never learned to work on cars and my mom wouldn’t dare let me have a motorcycle. “You got drunk and drove your car in to the neighbor’s house.” She scolded, “If you had a motorcycle you’d be dead!” She’s probably right, but in my defense, Fast and the Furious had a large impact on my teenage years. I still remember pulling my e-brake and screaming “TOKYO DRIFT!” right before I slammed into our neighbor’s chimney. But that’s a story for another day.

The nostalgic thought abruptly ends as soon as it had begun and I flash back to the girl in my bed. “Hold on a second,” I say, fumbling around in the dark feeling for the condom I laid on my night stand earlier in the evening. I gently tear the foil wrapper and remove the latex object I will someday grow to hate. Poking it with my index finger like the instructions recommend, I figure out which way the condom unrolls then slide it on. I am constantly terrified of getting this girl pregnant. After finishing this sexual conquest, I will surely take the condom to the bathroom where I will hunch over the faucet and fill it up like a water balloon. You know, so I can check it for holes, just in case. You never know when a trip to the pharmacy for some Plan B could be in order!

My alarm clock shines a dim red light across her body. I take in the site with a long gaze, then spread her legs apart and ease my way inside. At this point in my life I am a one trick pony, and that trick is missionary position. My strokes are short and slow, partially because I don’t want the bed to make a noise and partially because, well, I wasn’t endowed with a penis big enough to produce a long stroke. Luckily this girl likes me for my personality and not my frail body and lackluster genitalia.

As I am performing the lost art of missionary styled sloth fucking, I hear our house phone ring and muffled sobs start coming from the living room. I don’t let this deter me; I’m two minutes in to this deed and probably thirty seconds away from finishing. I am already breaking my own personal record for consecutive minutes spent inside a woman. “Come on Bret, hold on for another minute you fucking cock block!” I think to myself. 

I feel my testicles start to recoil as I prepare to embrace a rewarding feeling that I will later find out is termed “premature ejaculation.”

No sooner than I start to release my little swimmers, a knock comes to my door. It’s a knock I will never soon forget, it makes my butthole pucker and my hair stand up on end. I try to control my orgasm that looks more like an epileptic seizure as my mother opens my door. Turning my head, I try to shield my eyes from the light now pouring into my dark bedroom. “Fuck fuck fuck!” I repeat in my head reaching for my comforter that is wedged between the bed and the wall. I pull at it desperately to cover my naked behind but it is stuck. I am too weak to even make it budge.

“You have some nerve young man!” My mother’s voice is shrill as it cuts through the air like a knife. I don’t look up, I can’t make eye contact with her, I’m still busy pathetically tugging at the comforter. “Here I am nervous to the core, filled with sadness about my oldest nephew passing away³ and you’re in here having sex!” she scolds. I still won’t look at her, I’m too embarrassed, my focus is on the comforter. “You know what, don’t look at me. We are going to have a long talk later, mister!” she screams.

³When did ‘passing away’ become the polite way to say somebody died? I feel it’s correctly used when your grandpa takes his last breath of life while he sleeps peacefully in his bed. I don’t feel like it is correctly used when a meth’d out 28 year old drives his car off an embankment while screaming the lyrics to Motley Crues “Shout at the Devil” and the fucking car explodes. Just my two cents!

No sooner than the words leave her mouth, the comforter breaks free. With all my 130 pound might, I yank it away from the wall and it sails over our naked bodies landing right on my mother’s feet. “I’m sorry!” I let out as I jump to my feet without thinking, my dick and balls flopping around like they’re at a House of Pain concert. Mom cocks her hand back. “Oh shit,” I utter, wincing my face and preparing for impact as she slaps me twice. The lady has a hell of a left hand, my eyes begin to water.

“I’m so disappointed in you.” she says begrudgingly, the way only a mother can. She turns around, slams my bedroom door and leaves me standing naked, holding my left cheek in my hand and my manhood in the other.

I turn to face my girlfriend in the darkness of my room, my alarm clock casts a reddish glow on to my body, my voice perks up, “Did you notice I lasted longer than two minutes this time??”

Phildo and the Boondock Stains

Ask anybody that knows me and they’ll tell you I’m a huge fan of Craigslist. Perusing the Personal ads would make for a better first date then dinner and a movie. You can buy anything under the For Sale tab from pussy to a used Porsche, and one cannot forget the Rooms/Shared section. This is where I acquired a very special roommate in 2012. His name was Phil, and he was well, kind of a dildo. And that’s how eventually earned the name Phildo.

There’s nothing Phil liked more than talking about how shitty his life was and spending all his hard earned unemployment money on drugs and alcohol (and sometimes, rent). He was 53 years old with hollow eyes, a pock marked covered red nose, and a large wart that graced his left cheek leaving him looking like the male version of a drunk witch. He had no real family or friends and had a few lumps on his body that were apparently cancer. I felt bad for the guy but there wasn’t much fixing him; he was set in his ways.

Every morning started out with a six pack of Natural Light, a finally rolled joint (of weed from my stash that fucking mooch), and a half hearted attempt to find a job in the classifieds. (Let’s be real Phildo, you weren’t fooling anybody… we all know you had no intention of getting a job.)By afternoon Phil could usually be found passing out on the living room couch, still reeling over the Marmaduke he read six hours before. He was a simple man. Before crashing he’d always slink down to my basement bedroom to tell me a tall tale from his life, like that time he was supposed to be cast as one of the brothers in “Boondock Saints”, or the real secret to growing your penis four inches. I didn’t believe anything he said but did keenly listen to the penis thing… you know… just in case.

I would like to add that for the record, I lived in a nice carpeted basement bedroom, with a full bath included. I say basement bedroom and what usually comes to mind is a creepy, concrete dungeon with a single swinging light bulb. Well, I don’t have any windows, but it’s definitely not the kind of bedroom that makes you think, “It puts the lotion on its skin…” My dad came for a visit once and commented that my room had the stench of “Two wasted college degrees and fifty thousand dollars down the drain.” I think what he meant to say was, “Pot.” Also, he was not impressed by Phildo. “That guy is a loser.” I believe were his exact words. Such a hard ass.

Phil wasn’t a bad guy and there are things that I do miss about him. First off, he could find any drug you wanted; I don’t know how because the motherfucker never had any money, but he managed to come home with some very stellar items on more than one occasion. Not to mention, some of the best cocaine I’d ever smelled. (Get it? Smelled... ah, you don’t get it.)

                                                  

Second, the guy would run errands for cigarettes. Here’s how it’d work: I would ask for a gallon of milk and a box of HBO’s (Honey Bunches of Oat’s, fool) then watch as he’d fall halfway down the front steps and hobble like a pirate down the hill towards the grocery store moving in a way that I can only assume was a brisk jog. All it’d cost me was a couple menthol cigarettes and a dollar in quarters for the daily newspaper. That man loved his cigarettes, and he loved his Marmaduke. (And I loved to get high and not go to the grocery store.)

Well, with every good comes a bad, and with every rambling, should-be-homeless, drug addict roommate comes a negative. Phil only had one problem I could think of, that being he was the worst wingman in history. Seriously, a genital wart could have done a better job. A pubic hair desperately clinging to the edge of your toilet seat could get you more pussy than this guy.

TUESDAY: 11:00PM (I know it was a Tuesday, because that’s half price beer night and nothing gets my dick hard like a good deal.)

               

 “You want to go back to my place?” I drunkenly propose.

“Oh, you’re just saying that because you’re drunk!” Bonnie chimes.

“No… well, maybe. But come home with me now and let’s fuck! This is my final offer.” I reply.

“You are so forward, but okay… I’ll drive us.” Bonnie finally concedes.

               

Down the hill from our house sits a killer brewery that has two specialties: Great craft beer and hot waitresses. I enjoy a nice craft brew on occasion, but I really enjoy checking out a dozen beautiful girls. I’m too much of a puss to converse with any of them with the exception of the bartender, Bonnie. She stands just shy of 5’ tall and is… well rounded, both physically and in general. For being short, she has a rather long face with slightly sunken eyes complete with darkish bags underneath. Her smile gives way to an unhealthy ratio teeth and way too big of gums. Actually, let’s face it, the girl has a horse face.

Bonnie isn’t particularly attractive but this has made her develop an outstanding personality. Also, I feel it’s pertinent to mention that she has some sort of over active sweat glands. And this is not just me being an asshole, the girl sweats like a fucking hog. She’s bartends in a doo rag similar to Bret Michaels, she gets yellow pit stains in her work shirts, and twice now we’ve talked about prescription strength antiperspirant. (With conversations like this, how am I not sleeping with every girl I meet?) Bonnie is quite the sweaty, little tater tot, and really, the only unattractive girl at the bar. Most importantly though, she’s wants a short order of this sub-par penis and I’m ready to deliver. 

Fortunately for me, I find that a girl with a genetic flaw or two to be a turn on. Not because I have a deep rooted fetish for disabilities, crossed eyes or animal like features, but generally they have low self-esteem and never get any attention from guys. I’ll talk their (most-likely deaf) ears off. (Plus, I’ll take what I can get! Everybody knows that.)

I grin from ear to ear as Bonnie pulls in to our driveway. I rode shotgun, sitting on my hands, as I rocked back and forth in sexual anticipation. Slamming the passenger door, I meet her in front of our stairs and pick her up in my arms. Her greasy body is no match for me in my drunken state. Her clammy body slips from my grasp and slams to the concrete. Thank God she’s ugly or this could have been bad. She bounces (almost literally) to her feet and sweeps the dirt off her ass.

“Whoopsie daisies! I think I can just walk…” She says sheepishly.

This is her fault, I think to myself. Maybe had she fucking toweled herself off a little bit I could have vaulted her oily ass up there. It was like lifting a bowling ball covered in Vaseline with a horse face. 

Brushing off the incident, we run up the stairs and plow through the front door where lo and behold, there’s Phildo sitting on the couch, smoking a cigarette, watching Man vs. Wild reruns. He stands up and begins to  tell us something new and depressing about his life, I stop him in his tracks with a Shaq-esk box out.

“Not now, Phil!”

I point towards my bedroom and Bonnie bolts that way. I’m following in suit as a drunk Phildo begins a rant about how he could outlast Bear Grylls in a survival situation and hobbles behind me down the stairway. I ignore him assuming he’ll shut the hell up and stop pursuit.

I’m wrong.

He follows us in to my bedroom. Fuck this guy doesn’t give up. He begs me for fifteen minutes worth of company so he can get high (with my weed) before he passes out (for probably the fourth time today). I hesitantly agree after Bonnie gives me a shrug with a cheeky giggle, exposing those boner-killing gums of hers. I shudder in dismay and load a bowl.

“What about the hash?” Phil asks.

“What about it Phil?” I angrily reply. By this point, I am very annoyed.

“Well, can you just crush a little bit on top? I’ve had a rough day.” He claims.

“Oh for fucks sake.” I respond, sounding like my father when he found out I forgot my backpack on the drive to school.

My right eye twitches with irritation as I pull out my vile of hash and daydream of beating the old man to death with his Croc sandals. The old man being Phildo, not my dad. In my opinion, any seven year old that forgets his backpack two days in a row deserves a “For fucks sake!” Either that, or the ol’ Adrian Peterson ‘switchin’ treatment, which is certified by every grandmother in the lower 48.

While I load the pipe, I glance at Phildo. He is staring at me, licking his lips and rubbing his hands together like Tom used to while waiting for Jerry to exit his arch shaped mouse hole. I hand the pipe and lighter to him and he squeals with joy. Lifting it to his lips, he flicks the Bic and sucks on the pipe like I can only imagine a hooker sucks on a dick, long, hard, and deep.

The moment came and went as quick as a bullet and killed my sexual conquest in the same manner, Phildo took too big of a hit.

Mid inhale, his eyes roll back in his head as he drops the pipe and clinches his fists to his chest. He’s seizing. His body begins to quiver as he falls over, stiff as a board.  His skull collides with the wooden arm rest on my couch and he lies motionless on the floor with his fists still clinched at his chest. Bonnie shrieks in terror as I bend over with hands on knees frantically analyzing the situation.

My first thought: I need to drag him to the bottom of the stairs then call 9-1-1. “My roommate is drunk and he fell down the stairwell, I think he hit his head!” I rehearse the line in my head as I grab Phildo by the ankles.

Second thought: Bonnie will still want to fuck after the ambulance leaves, right? RIGHT??

“We need to call 9-1-1, we need to call 9-1-1!” Bonnie whines, sobbing through her hands mashed against her face. (Definitely not getting laid.)

“Shut up and open my door!” I retort, slowly tugging Phildo in that direction.

Just then, Phildo begins to flutter kick his legs like a child in a pool or perhaps, a woman in a Pilates class. I look to his face and see him blinking as he begins to glance around the room. “What the hell are you doing?” he asks.

“He’s alive, he’s alive!!” Bonnie yelps. (There’s still potential for a lay here!)

I drop his legs to the floor and slowly help him to his feet. Phildo is shocked at the story we tell him and is having a tough time grasping the situation at hand. He refuses a trip to the hospital even though Bonnie pleads for him to go. I know the son of a bitch has a concussion but there’s no way he’s going to the hospital, I’m not going to beg him to go. Instead, I pick up the pipe from the floor and offer it to him like a true friend. He declines it.

“I don’t want to be alone tonight.” Phildo says, carefully placing a hand on my shoulder.
“I understand buddy, you can sleep down here. Bonnie….”

“Yes, I better go… next Tuesday you come to the bar and I’ll buy you a beer, okay?” She cut me off mid sentence.

I comply and escort her to the front door. I give her a hug goodnight and reaffirm plans for next Tuesday. I shake my head walking down the stairs, “Fucking cock block…” I murmur to myself.

Phil eventually ran out of his unemployment and got evicted from the house we lived in. Every now and gain I think about him and miss his crazy tales and his uncanny ability to find drugs. I like to think he’s out there somewhere in a warm jacket with a Natty Light pounder, panhandling for money like a true survivor. And for the record, if Man vs. Wild was filmed on the streets of New York City, I think my man Phil could beat that cheatin’ son of a bitch any day.

Oh, and I ended up beating Bonnies guts in the following Tuesday. She laid there sprawled out like a starfish for the whole three minutes as I sexually ravaged her. It was boring, I’ve had better. Then again, I’m sure she has too.