The Adventures of Jake Cunningham

Hello, I suppose I should introduce myself before we get started. My name is Jake Cunningham and I am a twenty-six year old high school drop-out. I've been trying to get my high school diploma for a while, but honestly I'm just too lazy to get the work done.

I am 6'1" 151lbs. I'm very skinny, tall, and lanky. I've been told my appearance is skeletal. My skin is a very light brown or tanned. On occasion I've been told that I just look dirty. I have long, shoulder length brown hair. It's wavy, unkempt and unruly. I usually keep it tied back in a ponytail. I wear a pair of thin-framed oval glasses. My chin and upper lip is covered with wispy, peach fuzz. I've been told to shave multiple times, but I kind of like it. I think it makes me look rugged. They've said it looks like a strip of dirt but, I don't really care haters gonna hate, right?

I don't like to bathe or shower. I know some people find this disgusting, but I comfortable with my appearance. My friends and girl friend insist I shower a minimum of once a week. I usually adhere to this agreement.

My most impressive feature (I find) is my seven and a half inch penis. It's thick, uncircumcised and a couple of shades darker then the rest of my body. You might even call it brown. My hands are of comparable size. They've been called "freakishly large." I find they're about twice the size of a normal man's. My fingers are also unnaturally long and my knuckles are large and bony.

I've done a lot of stuff. If I was a liar; I'd tell you I wasn't proud of it. I've enjoyed everything I've done, even if it didn't win me any friends. I've been with guys, (mostly Bjs) and I've been with girls. I've fooled around with my sister and rode bareback with my cousin. I've even done stuff I don't want to mention. I once told a "friend" I was bisexual. He laughed. He told me: "You're not bisexual; you're just so pathetic you're willing to sleep with anything." I just consider myself open minded.

I think, I should state right now, that I really like to cum. I do it as often as possible. Right now I am nude, sitting cross-legged on my girlfriend's roommate's bed. I am typing on my girlfriend's laptop. Her roommate's panties are hung around my neck; I was sniffing the crotch of them while masturbating. I took them from her clothes hamper. She wore then pretty recently. I think they're from last night. Under the sheets I was stroking it, while looking at a photo of her and her boyfriend. When I came, I ejaculated into the roommate's face cloth. It is still damp from her shower less than an hour before.

I really dislike condoms. I hate how they feel. I hate how they desensitize me and I hate how they taste. I only use them very rarely. Except for the odd occasion I haven't used them regularly in about three years. I simply love cumming inside women. Ever since I first did it as a teenager, I've done it every chance I've gotten. I'm worried my sperm might be lazy. I've never gotten anyone pregnant. There was a period of about three months were I never used a condom. Nothing ever came of it.

I haven't gone to the doctor yet, because deep down inside I want to believe I'm still capable of making a baby. I like to think that when I cum inside a woman, with or without her consent, that I'm making her pregnant. I don't think it'd be the same if I knew the truth.

Following that description, you might find it difficult to believe I can get women. Getting them has never been that difficult for me. Keeping them is another matter. Usually women won't stick around longer then a one time fling. If they do, it's never anything more then "friends" with benefits. It almost seems as if they're embarrassed to be seen with me in public. I think there's a big misconception about women. Men think women are all high on themselves and like to pretend they have self-respect. I am here to tell you, you just need to push the right buttons and they drop the façade.

Occupation-wise, I don't exactly have a job. I don't have a car either, so any prospective ladies better live near a bus route. ;) Because of these financial restrictions I tend to live between three different locations. The first is my parent's house. The second is the homes of my various friends. The third (and most well traveled area) is my girlfriend's dorm room. It's in the residence of the local community college.

She is currently 21. We've been together about three years. She isn't from my hometown. She is from another city about two towns over. She used to have an aunt and uncle that lived next door to my friend. They moved a while ago. When we first met she was 16 and I was 21. I was dating another girl (who'd just turned 18), but from the moment I saw her, I knew I had to have her.

Her name is April Parker. I find it difficult to describe her. There are some things that can't be conveyed in words. I've always thought she was the most beautiful girl in the world. She is like one of those girls you'd see in an oil painting inspired by Greek or Renaissance art. She has the pale complexion, voluptuous figure, dark hair and innocent face. Her beauty comes from before the modern age. It's from a time before the modern conception of what is sexy or hot was ever conceived.

She is a big girl, but not too big. She is about 5'7" and weighs about 185lbs; but she carries the weight well. A large part of that weight can be attributed to her breasts. They are exceptionally large. I believe her bra size is 38I. Despite their size they sag only slightly and are surprisingly firm. Her potbelly protrudes slightly, but it is overshadowed by the girth of her breasts. Her shoulders are narrow and her hips are wide. She has thick thighs and large buttocks, yet nothing seems out of proportion.

She has luxurious long hair that cascades down over her shoulders. It is thick and straight. It was originally a medium shade of brown. Recently, she attempted to dye it blonde. The result was a brassy color with dark brown roots. When the light hits it a certain way, it shimmers with an otherworldly sheen.

Her skin is beautifully fair. It is smooth, soft and flawless with a light dusting of peach flesh tones. Her eyes peer out from behind a pair glasses. They are oval shaped with thin metallic frames. Her eyes are bright, intelligent and easily excitable. Their shade is a light piercing green. It is so brilliant that once you glimpse them you can't look away.

Her prettiest feature is her face. It is gentle and round, with a slight double chin. She has these cute, chubby cherub cheeks. It is definitely a baby face. Her smiles are bright and brilliant. She is always smiling. She projects an air of innocence. She is pure, simple and good-natured. It is almost as if she were a little girl.

Her voice is similarly young and cheerful. It is little and cute, but not to the point where she sounds annoying.

There is a point of disagreement between April and I. She is deathly afraid of getting pregnant. She thinks that if she gets pregnant, she'll have to drop out of college. Her parents have told her they are only paying her tuition once. Neither she nor I have the money to pay a second time. There was a long time where she could afford birth control. She didn't get a lot of work during college and eventually we had to stop buying it. For the past four months or so, I hadn't cummed inside her. As you can guess, it was eating me alive.

Now, I love my girlfriend very deeply, but I cheat on her regularly. I guess not regularly, but I never pass up a chance to get laid. To me variety is the spice of life and I just can't stand being restricted to one woman. April doesn't have any idea, either. Every time she goes back home to visit her parents, I sleep with at least one other person. It's always completely unprotected unless the woman insists on using a condom. I know I should be concerned about STD's, but I figure April is going to be with me forever. What does it matter if I give her something?

I know that April will believe I am cheating on her. She always trusts me more then anyone else. She even trusts me over her parents and close friends. One time I was having this three week fling. It was with one of April's close childhood friends. The friend tried to tell her about the affair, but I convinced April otherwise. One time the friend lied to April to protect her feelings. I used this to convince April that her friend was a pathological liar.

Needless to say, the friend's gone and I'm still here. I'd still sleep with her though.

I'm afraid I've gotten off-topic. I wanted to tell you what happened between April and me last night. The roommate had gone out for the evening and we knew she wouldn't be back until after midnight. April was staying late at the college doing additional work, while I lounged around watching TV.

I was thinking about how few cream pies I'd made in the last few months. April and I do a ton of stuff (She hates anal though). But, none of it had the satisfaction of cumming inside her pussy. I'd gotten some blowjobs from other girls and a round of vaginal sex, but I had to wear a condom. No matter how hard I tried, I couldn't convince these girls to do bareback.

I thought about this for a while. Then I considered ejaculating inside April without her permission. At first, it was a joke. I laughed it off. The thought persisted, however. After an hour and a half, I'd decided I was going to cum inside her.

Around nine O'clock I heard a key jingle and the door opened. My beloved April came in. She tossed her backpack and purse onto a chair by the door.

"How was your day, honey?" I asked. As I spoke my eyes ran over her figure.

She wore an incredibly tight, blue T-shirt. It was the type of shirt fat girls were advised not to wear. It clung tightly to her voluptuous figure. It illustrated a clear definition between her large breasts and her pot belly. I must re-state, how well proportioned she is. Despite her very large breasts and extremely curvy figure, nothing appears disproportionate. It's like she has the most of everything you could have, without going overboard. Despite the fact her breasts are ridiculously large; they still seem to fit within this beautiful masterpiece of the female form. The shirt had a very low neckline that revealed almost all of her generous cleavage. Whenever she moved, no matter how tiny the movement, her breasts would jiggle noticeably; they couldn't help but draw attention. When she walked down the halls, everyone looked. This included the tough jocks that preferred blondes who were nothing more then tits on sticks. Even other women looked out of jealously or lust.

I know she likes to play cool or pretend to be coy. She acts like she doesn't realize how visible they are, or that she doesn't like the attention. Deep down inside, I know she loves it though. I know, because whenever I give her a little alcohol or a little weed I can get her to flash anybody or let complete strangers suck on her tits.

When she's sober she tells me she loves me. She tells me she could never imagine being with anyone other then me. When I get her drunk enough she's all to eager to suck off other guys the moment I mention it. Once I even got her and my best friend to start fucking a little. The booze wore off before either could finish. I wanted them to finish though; I wanted to see him cum inside her. As they started to become reluctant I even considered grabbing her ass and forcing them to continue. I was sobering up though and I worried she would get offended.

In the apartment I continued to examine her. Her jeans were unbearably tight. Her thighs, hips and buttocks looked massive. It was as if they were painted on. I don't even think she could use the pockets. Above the waist of the jeans, a small bit of muffin top peeked out.

"It was alright, a little frustrating." She said quietly as she emptied the contents of her bag onto the table. She rummaged for a bit, and then threw her head back. She whipped her hair out of her face and stood up. She looked at me. A stray lock of hair fell over her eyes. Effortlessly she pushed it back.

She smiled; it was the same smile I'd seen a million times before. It never lost its brilliance. She seemed young, happy and innocent. All the memories of the things she'd done seemed wrong; it was as if I'd lied to myself. She was no longer the girl who gave her boyfriend and his best friend simultaneous hand jobs after downing tequila. She was just a young girl who didn't know what sex was.

She approached the couch; it was as if time slowed. I hate to make this sound sappy, but she was the most beautiful thing I had ever seen. It was like I was Adam looking upon Eve for the first time.

"What's with that look?" She asked playfully, her smile never wavering. Suddenly her eyes changed. It was like she knew exactly what I was thinking. She knew I wanted to fuck her.

"Let me see your hand." I said.

She extended her arm without hesitation. Her hand hung limp. It was small, pale and plump. Her fingers were tiny, almost stubby. Her nails were painted a deep, metallic purple. Even though they were small, they were still beautiful. They were half the size of my own. When these tiny little hands held my cock, it looked massive.

I gently took her small hand in my own and kissed it.

"Awww," She cooed and her smile widened. It sounded odd, like she only half meant it. She leaned back, biting her lower lip. It was as if deep down inside she wanted me to cut to the chase.

Gently I took her hand by the wrist. I moved it down, pulling her forward. She leaned over, I could see clearly down her shirt. I pulled her further, positioning her hand over my crotch. I placed it on the bulge of my jogging pants.

She gave out a cute, little girlish giggle.

"What's this!?" She exclaimed childishly as she felt my penis through the fabric of my pants.

I simply smiled at her. She continued to feel her way around; she gripped it tightly until it began to stiffen.

"Take off your pants." I commanded.

She looked at me for a moment. She seemed unsure of what to do. She stepped away from the couch and began to pull her T-shirt over her head. I licked my lips with anticipation. She slowly unbuttoned her pants and began to pull them down.

I stood up and approached her. She removed the jeans from around her ankles. Before me she stood, in nothing but her bra and panties. As I drew closer her eyes grew wide. In the fluorescent light of the dorm they seemed to tremble. I gently placed my large, tanned hand on her pale throat.

She remained motionless. She appeared paralyzed with fear. Through her glasses, her beautiful eyes appeared slightly magnified. I felt her swallow hard.

"Who owns this pussy?" I asked, the question was rhetorical.

"You do, Daddy." She whimpered quietly.

"I love you," I said as I leaned in closer.

"I love you too, Daddy." She replied.

I kissed her on the lips. Our mouths opened and our tongues danced across one another. She tried to pull away, but I held her tight. She was no longer coy, she was no longer innocent. I was the spider and I'd caught her in my web. Now it was time to reap the rewards.

As she resisted I pressed my pelvis to hers. Our genitals rubbed against one another through the fabric of our clothes. I pressed more firmly and she jutted her pelvis forward in reciprocation. As I became more aroused my penis continued to stiffen, encouraged by her body movements. I could also tell she was quickly becoming aroused.

After a prolonged amount of dry humping, I broke our kiss and pulled away. Her mouth hung ajar. She had a vaguely dazed expression. Her glasses had begun to fog.

I reached behind her. I felt the soft, smooth flesh of her back. With a quick twist of my wrist I unfastened her bra. It fell slightly. She quickly removed it, exposing her large, beautiful breasts.

I took one in each hand, examining them. As I noted before they are surprisingly firm. I believe this is because they are mostly breast tissue rather then body fat. They were also very round and held their shape well. They sagged only slightly. In the center of each, the milky white skin took on a peach pastel hue as it approached the nipple. A single brown mole sat about an inch above the left nipple. It was the only landmark of the pale landscape.

I looked up from her breasts. She had turned away from me and was avoiding eye contact. I always thought she felt self-conscious of her breasts. This was especially apparent while nude. She told me once of an incident in her last year of high school. For an end of the year trip, her class had gone to the beach. While swimming in the surf she'd lost her bikini top. Her breasts were fully exposed. Everyone in the class saw.

She frantically tried to cover herself. Then she tried to find the teacher. However, the teacher had disappeared into the woods. She tried to keep herself covered. After a few male students tricked her into exposing herself a couple of times, she gave up. The teacher returned about forty minutes later. She found April sitting at a picnic table topless, eating hotdogs. A number of students took pictures with their cell phones. They eventually made their way around the school. She received a ton of nicknames and she couldn't walk down the halls without being propositioned. Her parents were very upset.

I took April and held her by the chin. Gently, I lifted her chin until we made eye contact. She looked at me with uncertainty. Then once more she smiled and we continued to kiss.

I took her back to our bedroom. I stripped off her panties along the way. She lay across the bed, on her back. There she lay, completely relaxed. She had a smile upon her lips. Her large breasts lay almost flat against her body. Moonlight poured through the window. It washed over her pale form. I could see her nude body in all its glory. I saw her chubby arms, wide hips and noticeable potbelly. I salivated over her large breasts, chubby face and slight double chin. A small bushel of brown pubic hair wreathed her vagina.

I leaned forward and began to suckle her pastel pink nipples. I grasped her very large, firm breasts. I took one in either hand and began to grope them. I continued to lick and suckle. I teased her nipples with my tongue until each one stood erect.

Gently she placed her hand at the base of my skull, encouraging me. As if she was nursing me. I continued to suckle. I squeezed her breasts softly, then more firmly. She extended her legs and arched her back under my weight. Small, soft groans escaped her lips.

I stood up again, removing my jogging pants. I stood there, in my boxers. My penis stood fully erect, its outline protruding from my boxers. I remember the first time she saw it. We weren't dating then. She was surprised. I was the biggest she'd ever had. She was even more surprised when I came inside her. We'd only met a couple of times before and I had a girlfriend. She thought we were only fooling around. That was when I found out she was really scared of getting pregnant. For about eight months I never heard the end of it.

I stripped down completely nude and got on the bed. As I lay on my back, I placed my hands behind my head. . She began to stroke my penis while she leaned over me. Her large breasts dangled in my face. She crawled down and began to kiss the top of my stomach, above my navel. She kissed her way downward. Her lips moved along, the thin wispy trail of hair that ran down my stomach.

She stopped just before she reached my penis and looked up at me. With my dick in hand she gave me another big, girlish grin. My penis was incredibly hard. It throbbed with pleasure, aching to be released. She was squeezing it as hard as she could. She stroked it again and again. She gave me one final girlish giggle and then she bent forward. My large, thick, brown uncircumcised penis began to slide between her lips.