The Pain of a Nineteen-Year-Old Virgin

Collection of Dildos

At 19 years of age, two years out of high school, and my last year attending community college fast coming to conclusion, my ass ached sitting in the bathtub. I attempted to relieve the inflammation, pain and swelling in my ass using Epsom salt in the warm bathwater. The pain had started to subside somewhat. I knew why my boss discontinued and discarded the huge black dildo line, just too fucking big for man or woman.  

I couldn’t believe I’d amassed such a large collection of dildos, porn videos and other sex toys since I began working at the adult sex store. By all accounts I could be considered a virgin; although, I’d never engaged in sexual intercourse with a female, my ass fucked the shit outa dildos and of course I’d pleasured myself by hand over the years. 

Even though a technical virgin my more active repertoire and vivid sexual imagination bested most young people my age. I needed an active imagination because my redheaded sex mistress, the Ice Queen, resided in a dormitory room half a continent away, where the sultry seductress attended college. Oh, how I longed for her to suck my big cock again. Since she departed for college no more blowjobs. The extent of my pent-up sexual frustration had been hammered out by hand with the help of my collection of sex toys and porn videos. 

During the early months of our separation I satisfied my sexual frustrations by way of masturbation. Masturbating to thoughts of fucking my beloved Roseanne. I dreamt about her sucking my dick to fruition; however, after the first year apart those memories began to fade. After high school graduation, with the help of my parents, I got my apartment and landed my secret part-time job at Ye Olde Adult Sex Shoppe. I would lie in bed of a night watching porn videos fucking myself to fruition with different dildos, some battery powered models. 

Fast becoming a sexual hedonist, I began contemplating the question whether pornography, masturbation and dildos had become somewhat addictive. Since moving into the apartment, I whacked off three, four, five times a day, sometimes more on weekends. I would beat my meat in secret at school or work thinking about girls; however, of late, boys for some reason. My mind had become occupied 24/7 with thoughts about sex since moving into my apartment. 

Why not? I worked in an adult sex shop. After graduation from high school my parents paid the security deposit on the apartment where I resided to help me get on my feet. They also paid half the month’s rent each month for the first year on the small apartment close to college, or until I got a job, whichever came first. I’d kept the job at the sex shop a secret, so my parents continued paying my rent and would not find out where I worked. 

Being that my family conservative and religious there didn’t seem to be a chance of discover. Although the community college campus in my hometown, my parents thought I needed a place with some privacy away from my younger siblings, where I could concentrate on my studies. The apartment located within walking distance to home, work or the campus provided me privacy to pleasure myself at will. I carried a full load of classes my freshman and sophomore years while working part-time at the adult store job my second year. The hours at my job provided me quiet space to grow where I could complete my homework and projects without interruptions. 

My goal when I transferred to state college in the fall, graduate with a dual degree in Journalism and Media Communication. The boring prerequisite courses at community college were cheaper than state, so I took those classes at community college in preparation to pursue the final degree program at state. All my classes required me to do much writing and research. I moved out of my bedroom that I’d shared for years with my younger brother who had just come into puberty: a win-win for all parties.  

The day I moved I borrowed a van from my dad’s business, packed up most of my belongings, including my new high-end computer, and moved into the one-bedroom apartment about midway between home and the community college campus. That’s when a whole new world of sex opened to me like Pandora’s Box: an invitation for a fresh eighteen-year-old boy to lose his virginity. I began collecting sex toys. 

That summer after my freshman year working at the sex shop gave me the funds and opportunity to set in motion my quest to lose my virginity. By my second year I’d yet to lose my cherry to a female or male; however, my virgin asshole had been assaulted and penetrated by many dildos over that period. Something I’d come to enjoy. I enjoyed being a bottom. 

Early that May morning my ass smarted from that previous painful encounter with the extra-large dildo, an item discontinued at the store. My eyes glued to the porn video playing on the large flat screen computer monitor. While I stroked my hard cock, my heartbeat increased as sweat began to drip from my body. The formidable porn actor on-screen captivated my attention: my lust for him undeniable.

The freckled ginger actor’s lithe body possessed great athleticism and the most beautiful cock I’d ever seen. His body mass index below normal he had a thin waist, his chest, arms and legs were all well-toned. Not a bodybuilder muscle man, but he knew how to take care of his body. From what I could see his flaccid long thick veiny cock probably topped out at least seven inches erect, maybe more with a luscious prominent pink glans. The more times I watched the video the greater my desire for the fire crotch actor. 

Every time I watched I wished for him to jump off the screen into my bed and fuck the shit outa me—fuck me senseless. 

Of course, wishful thinking. The computer system had been a graduation gift from my grandparents to do college research and write academic papers. My grandparents would have been shocked to death knowing the high-end Macintosh computer they’d given me had been turned into a sex machine to gather pornographic material for my sexual gratification. Oh, sure there were academic programs on my computer, but the machine provided me with an excellent opportunity to investigate and then store pornography that I discovered on the Internet. 

The Internet had been a godsend for many youths. I could call up porn with an instantaneous touch of my finger to the keyboard. That’s why that spring morning a few days after stretching my asshole beyond normal limits with that larger than life dildo I decided to turn on my computer, call up my favorite male porn video actor and watch him while I rubbed one out before starting my day. 

With the touch of my finger on my right hand to the keyboard I sent a command to the machine, prompting the operating system to summon up the video file of choice, which lit up the large flat screen. I watched the video with lust while I lubed up my cock with my left hand and began caressing it. With deliberate and delicate strokes, I watched the two males perform, ending in an explosive anal intercourse scene. 

I watched with delight while my all-time favorite ginger actor cornholed his on-screen partner, fantasizing about me as the one getting fucked. During that time caressing my cock, I paid special attention to my glans. As far as I was concerned, the glans was the most beautiful and most sensitive area of the male appendage. I considered my unencumbered glans a work of art with its bulbous spongy pink cockhead and even more prominent crimson coronal ring: much like the on-screen actor’s cock, just a little smaller. My mushroom cockhead appeared a cross between the standard and helmet cockhead. 

The doctor who performed my circumcision a couple days after birth had been an artist creating a true work of art. I held the six- and half-inch shaft in my left hand while the saliva wet forefinger on my right hand circled the coronal ring at the base of the bell cockhead. My forefinger kept circling the coronal ring before touching the frenulum area. A smidge of clear fluid began to appear at the piss slit. I knew full-well the oozing precum meant a forthcoming ejaculation, but I wasn’t ready to cum. I released the grip on my cock shaft and moved my hands to my pecs where my fingers found two erect nipples that needed attention.

Another reason why I enjoyed the ginger actor on the video I watched, his nipples. Unlike many vids the two actors paid attention to each other’s nipples, their cocks remained hard while they vocalized pleasing each other. The dark-haired guy paid special attention to the redheaded guy’s nipples, making him moan with pleasure. The ginger actor, like me, displayed prominent pink nipples that became hard as diamonds when stimulated. 

With my thumbs and forefingers, I began to titillate both firm sensitive pink buds in the middle of my larger darker areolas. Oh my, the feelings in my nipples being stimulated brought goose bumps to my body. Electricity traveled from my nipples to my cock and vice versus.

I threw my head back moaning as I experienced the pleasure of nipple stimulation. After a few minutes playing with my nipples the forefinger on my left hand found my sensitive asshole while the other hand returned to my cock. With my right hand surrounding the shaft of the engorged slick member I dreamed a pair of warm wet lips engulfed my cock. Then the ginger actor’s tongue began circling my corona, all while getting finger fucked. After a few more drops of cherry flavored lubricant I continued stroking my member to fruition. I listened to the two actors squeal with delight moaning with passion as they satisfied each other.     

With spooge all over the front of my body I got up and walked towards the bathroom. After my shower I sat on the side of the bed preparing to put on my socks and shoes. As I slipped on my brown loafers on my mind raced back to that day when Phil and I first compared cocks as kids. My long-time best friend Phil who had been blessed with auburn hair and I attended school together since fifth grade.

I remembered the day, that summer between sixth and seventh grades, when he opened the door to my bedroom and walked in unannounced. He caught me red-handed beating my meat. He didn’t appear surprised; instead, he closed the door, turned the lock, opened the front of his Levi’s, and then asked, “Do you mind if I join.”

Although he’d caught me by surprise, I had no qualms about us jacking off together. Phil and I had seen each other’s naked bodies many times before, but not in a full state of arousal during our youthful years. Those days were in the past. We’d skinny dipped with others down at the river throughout the years, and of course seen each other naked showering and changing in my family’s pool house after swimming as well as the school facilities while participating in sports. 

Since the first time I got a peek at Phil’s nakedness I’d become aware that he was hung a little better than me and most of our friends; at least, as far as flaccid length. By 12 years of age, almost 13, his limp uncut cock appeared to hang between four to five inches long; whereas, mine hung about half that length flaccid, but I imagined us both to about the same length and girth erect. I had never seen him fully boned up before.

Neither one of us said another word for a few minutes we just stared at each other’s hard dicks on the sly. With great caution I studied Phil’s dick. His was a little bigger than mine. I noticed that his foreskin appeared to be very tight around the glans, so tight that he could not pull it back exposing his cockhead. That must have been demoralizing and why he manipulated his manhood in such a careful manner. All I could see of the hidden head, about the first third of the glans: only the piss slit, and the tip of his purplish cockhead were visible.

Over the waning days of that summer of our youth we continued to stroke our dicks together. We would meet in my bedroom or other hideaways to jack off together. I secretly yearned to touch Phil’s dick, but I knew better. One day in the basement during Christmas break Phil pushed his Levi’s down to his ankles kicking them off so he could spread his leg to get more comfortable. I got up step out of my Levi’s and drawers before I walked over to lock the door.

When I returned to the couch Phil surprised me. He reached out and touched my dick saying, “That’s one nice looking dick, especially the head man. Sure, has grown the past months, huh?”

“Thanks.” 

“I just wanted to feel it…Not queer or anything. I guess I’ve just wanted to feel it for months,” Phil said. “Sure, wish my foreskin would pull back so I could see and feel my cockhead.”

“Yeah, from what I can see looks like you’ve got a really nice-looking cockhead buried beneath that skin.”

“Maybe one of these days when I get older, I’ll see the doctor about getting the tight skin taken care of…Then maybe you’ll get to see it.”

“That’d be cool. So, does it hurt to fuck a gal or get blowjob with foreskin so tight?” I asked.

“You know, sex is sex, hand, pussy or mouth, whatever the chick wants to do…All I’m interested in is getting a nut.”

“Cool.”

“So, Ran, you ever had a blowjob or fucked a chick?”

“Nope, not yet.” 

“What about guys?” Phil asked. 

That question surprised me. “Nope, no blowjob…Never had sex with a girl or guy,” I said. If Phil was only aware of my fantasies and dreams that included him.

 “So, what about you?” I asked.

“Sure, I get blowjobs all the time…Got this chick that sucks me off.”

Somehow, I figured he might be lying, but I let it go. I reached over and began touching Phil’s dick; it felt different than touching my own, so soft, satiny, and warm. I hoped that my touch felt as good to him as his had to me a few seconds prior. Again, Phil warned me to not force the foreskin back when I stroked it. Damn, my friend had just given me the green light to stroke his cock. 

I manipulated Phil’s dick with tender care not wanting to cause him any pain. Within a few seconds Phil once again touched my cock. Oh damn, I watched with longing as he touched my hard cock. The feeling of his hand and fingers on my dick gave me overwhelming pleasure. By this time, we’d turned facing towards each other on the loveseat to get more comfortable.

“Feels good huh?” Phil asked with a smile, “I love it when my girlfriend plays with it…She’s got such a soft touch, but even better when she sucks on it.”

Both of us were enjoying each other’s touches, making light moaning sounds of pleasure as we manipulated each other’s rock-hard cocks. I wanted Phil to go down on me. I let my fingers roam to the base of Phil’s long dick through the tight dark patch of curly pubes. After I played in his bush I advanced to his scrotum. I began feeling his balls gently rolling each one of them around in my fingers as I gazed upon his smooth body. He moaned. 

Phil’s olive colored smooth skin dark and well-tanned with no hair and not a blemish on it; whereas, mine was paler, creamier. I had discovered that the Italian male’s skin to be darker, while Irish guys skin color tended to considerably lighter. Phil being half Italian with emerald green eyes that were stunning looking intrigued me. Both of us tall for our ages weighed about the same. We sat there in silence admiring each other’s bodies and hard cocks. We seemed to have forgotten about time as we explored each other’s the genital areas. As I looked down, I noticed that my pink nipples were engorged: the buds standing at attention on my chest.

About that time, I heard the door slam. It was my sister. Phil and I got dressed in a hurry, pushing our cocks down our trouser legs trying to conceal our erections. Whatever had almost happened would have to happen at another time. Returning to reality I entered my kitchen and fixed a bowl of cold cereal for breakfast before heading off to work and then to college classes in the afternoon. When I got to work at Ye Old Adult Sex Shoppe my boss greeted me saying, “Got run Randy…Breakfast meeting with marketers. Take care of the place this morning.”

I busied myself around the shop rearranging displays and cleaning the glass cases. The shop considered a high-end adult store in town had no booths for viewing porn or glory holes to lure perverts. One large room filled with nothing but CDs, videos and magazines. The smaller main room up front contained locked glass shelving with sex toys, lubricants, soaps on ropes all the stuff to make either heterosexual or homosexuals tryst complete and gratifying.

After the boss left that morning there had been about half dozen video rentals and a couple sales, mostly videos. Then I noticed the only person left in the store: a gorgeous young redhead. I waved at the customer as he continued to browse. I thought I recognized him but dismissed the thought. Occasionally, as he looked around at different items, he would glance a fleeting look in my direction. Of course, I’d been checking him out too.