The Pain of a Nineteen-Year-Old Virgin

Agonizing Pain

“Yeoooooow!” Searing pain shot through my body. 

The agonizing pain in my ass scared the fuck outta me as I awoke. My cold naked body shivered and convulsed with agony. My simple bed soaked in body fluids, reeking with the stench of anal sex. 

“Oh shit!” I exclaimed. The odor of stale perspiration as well as tinges of fecal matter and urine penetrated my olfactory system. Once again, I attempted to roll over towards the edge of my bed to get into an upright position; however, the burning throbbing sensation in my asshole, prevented such movement. I lay there motionless, my head ached, ready to explode, on my right side, atop damp bed sheets. Again, I cried out in agonizing pain, “Ow fuck. Oh fuck.” 

A stinging pain of fire filled my ass; it felt as though someone jack hammered a telephone pole up my butt hole all the way to the pit of my stomach. The smell of raw sex permeated the air that morning, while an unpleasant odor of stale feces and urine filled my nostrils. As I looked around the comforter, top sheet and pillows all missing. I could feel the front of my body down to my crotch area covered with a gooey substance. 

  Once again, I attempted to upright myself on the edge of my bed; however, I concluded that the huge item hammered up my ass prevented such a maneuver. The pain became more intense each time I attempted to move, making it near impossible to sit up. I looked around the room at my surroundings to make sure I was in my own bed, my own bedroom. 

Sure enough, my bed, my room, and then it dawned on me I’d just finished one of those terrifying demon driven dreams; night terrors if you will, where I’d been fucked up the ass by Incubus a homosexual demon with a humongous dong. 

Surreal dreams that occurred almost every night for past weeks became more intense with each occurrence and progressively larger dildos. Since I started to work at the adult sex shop, I’d amassed a large collection of dildos and pornographic videos. I stored the sex toys and videos in my armoire. A tall dark wooden antique cabinet that housed my entertainment center. I filled the cubbies and drawers inside with items of pleasure. Aware I had to get to work I tried to get out of bed again.

 Finally, with great care I managed to get to my feet; unsteady, I stood next to the bed, holding onto the trusty headboard for support. My feet spread shoulder width, I bent forward at the waist, reaching between my legs for the object lodged up my rectal cavity. I grasp the bulbous base of the rubber sex toy and attempted to dislodge the huge black dildo from my asshole. Because of a tight seal formed by my sphincter muscle surrounding the larger than life dildo the rubber toy refused to break free. 

The rubber phallus, at least the thickness of a standard size beer can, remained. No matter how much I tugged on the large rubber balls the base of the dildo it didn’t break loose. As I attempted to wrench the fake penis free from my rectum I questioned, how my ass, or anyone’s ass, for that matter, could endure something that fucking big? I envisioned the embarrassment I faced having to call 911 for paramedics to transport me to the ER to have the huge black dildo removed from my ass.

As I stood there, I began to question the validity of porn videos I’d viewed and stories I’d read about guys sucking on massive male members or getting fucked in the ass by men with enormous cocks. On more than one occasion I had attempted to suck and fuck couple of my larger dildos. I couldn’t take the entirety of those huge rubber dicks all the way to the base as I had read about or seen on videos. Maybe I just had small mouth and ass.  

Finally, after moments standing next to my bed implementing mind over matter technique, I coaxed my sphincter into relaxing its grip on the immense rubber toy stuck up my ass. With the vacuum tight seal broken I almost lost my balance pulling the huge dildo from my ass. A thunderous clap could be heard echoing throughout the confines of my bedroom. The thick ten-inch-long black dildo exited my well lubricated rectal cavity. I couldn’t maintain my grip on the slick heavy rubber dick; therefore, it fell out of my hands hitting the floor with a resounding thud, bouncing around the floor between my feet, followed by the unmistakable sounds of longwinded flatulence. 

 Once I regained my sense of balance, I stood there weak kneed wobbly. The feeling of outside air rushing inside my gaping asshole shocked my senses. I pondered my next move as the crazy sensation of the cold air rushing up my ass began to subside. I began walking towards the bathroom at a slow-moving methodical gait. 

The pain in my ass forced me to take slow deliberate steps towards my bathtub. I drew a tub of warm water, poured in a couple cups of Epsom salt to soak my aching burning ass to ease the pain in my bottom. As I sat in the tub my bottom began soaking up the benefits from the magnesium sulfate solution. After a few minutes I prepared the washcloth in my hand with scented body wash and began scrubbing my face, moving to my ears, neck and under my arms before washing my chest with a sparse dusting of blonde hair in the upper middle area of my chest. 

The washcloth stimulated my pink nipples as the terry cloth rubbed across them. I dropped the colored cloth into the water. My fingertips found their way to my erect pink buds where my forefinger and thumb on each hand began flicking and tweaking each nipple. As usual, electricity shot through my body to my cock while titillating the engorged nubs. Then I eased my hand below the waterline.

Underwater I discovered my erect cock; however, my hard cock not the item that piqued my curiosity. I let my hand move past my cock, holding my ball sac aside I began examining my aching ass hole. With ease I slid my middle finger up into the tender cavity as far as possible, fingering inside my rectum. Searching the anal cavity to make sure I’d not damaged the inside. I needed assurance that all the old lube and fecal matter had been expelled and I’d sustained no injury. After I pulled my finger from my anal cavity, I began to smell it, no scent of shit. 

As I continued sniffing my finger, I thought about my dreams. For weeks since working at the adult store I had been plagued by sexual fantasies at school, work and when I got home. The mind bending nightly erotic dreams drove me to lube my ass pushing much lubricant inside my ass. Then I’d fill my inviting ass with a new phallic toy for a night of dreams about me being seduced by different good-looking men I’d met throughout the day. Of course, all gifted with larger than average endowment. I dreamt that we engaged in all sorts of erotic sexual activity together, all the stuff of which porn stories and videos are made. One porn actor that grabbed my attention: a ginger actor for which I’d developed great affinity.

The videos featuring a twenty something redheaded Rascal actor with freckled face and upper body captivated my attention. He possessed the most beautiful cock I’d ever seen. Often, after putting one of his videos in the DVD player housed in my armoire, I’d lube my ass and insert one of his dildos, pretending to get fucked by him. My dreams would culminate by me getting fucked up the ass by this redheaded actor to fruition: an explosive orgasm. 

I’d never given much thought to being homosexual because I had a girlfriend, yet curious why erotic dreams about sex with men, especially this actor bowled me over with lust. Since I can remember I’ve been a voyeur. I have always had a penchant for watching boys and young men with beautiful bodies and cocks as well as the bodies of girls and young women. 

My dreams seemed so real playing out in my head in bed of a night. Roseanne my former girlfriend, the ravishing redhead, had long since faded from my erotic dreams replaced the well-hung ginger actor. The girl with alluring green eyes whom I’d been dating since high school no longer provided me that modicum of sexual relief, we’d experienced throughout our high school days. I missed her, instead I’d traded her for sex toys and dreams about a redheaded porn actor. 

Roseanne a prudish girl never allowed me to go all the way. Her knowledge about sex intrigued and overwhelmed me from our first sexual encounter during my freshman year in high school. As my mentor she allowed me to kiss and suck all over her body; furthermore, she’d suck my sensitive nipples, my cock and balls until I could go no further, but no pussy penetration. 

I had no sense of self-control during those early teen years; thus, it didn’t take but a few minutes of Roseanne pleasuring me till I got off. 

A year younger than Roseanne, who at present was about to finish her third year in college I’d had been a grade behind her in school. My beautiful redheaded sweetheart, a chaste Catholic girl, wanted to save her virginity for marriage. Me, on the other hand wanted to ease my adequate cock into her succulent virgin vagina, you know, just try it out, test the water before commitment to marriage. 

Although Roseanne did not hesitate to suck my cock or let me go down on her beautiful pink vagina to lick her pink pussy lips and then suck on her clit, the redhead allowed no penis penetration. She did allow me to take my cock in hand rubbing my cockhead, oozing with precum, over her clit until I ejaculated warm cum all over that strawberry; however, once I climaxed I had to make a quick trip south to her portal of love where she forced me to lick it clean of all my juices. 

When aroused her luscious clit would swell up the size and color of a strawberry and it tasted just as sweet. We would sixty-nine until she orgasmed. We did just about everything sexual together, but she would not let me penetrate her pretty pussy topped off by a well-trimmed red bush, even using a condom. 

Back during high school days, while her parents worked, we would come home from school, go straight to her room and pile up on her large bed with white linens. Instead of doing homework we stripped down to our underwear and make out all afternoon. We would work up to a high state of sexual arousal. She allowed me to titillate her voluptuous body, kissing on her ample breast and sucking on her firm brown nipples. Then she demanded I devour her pussy, but no penis penetration. 

Hell, she would allow me to do just about anything and everything, except let my cock pass the self-protected portal of passion. Roseanne defended that treasure with everything she possessed. She allowed me to dry hump her to climax while we kissed. Once she climaxed, she recovered quicker than me. She would lie on the bed next to me teasing my body, playing with my nipples. Of course, she would finger her clit to get off a couple more times before I regained my libido. As a young hot-blooded male teen, I possessed good recovery; however, as I look back, I think my infatuation with boy’s penis and erotic dreams about sucking cock and anal intercourse all began much earlier than sex with Roseanne.