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Comments and critics on the story are welcome and may be directed to E-mail: bn2rumpranger "at" yahoo "dot" com Subject line: Latchkey Kid Turns a Profit
Latchkey Kid Turns a Profit
By Randall Rumper
"Oh Yeah! Fuck me Jimmy," I growled as I rode Jimmy Connor's hard hot cock that was buried deep inside me.
Five other boys from sixteen to twenty sat around the room watching Jimmy fuck me in the ass as they waited their turn. Before I began fucking Jimmy there had been an oral orgy among all of us on the big hotel room bed. My sister and Jimmy's older brother moved around the room directing the action and video taping the event from two different view points. They weren't making pornography to sell to the open public; however, the video tapes would be edited, and for a fee each of the participants would receive a copy. After the oral orgy concluded all six had drawn randomly to determine the order in which the boys would take turns fucking me.
To my delight Jimmy won the draw. I promptly mounted my best friend and been impaled on his throbbing hard member for the past few minutes awaiting the stroke of midnight -- the ball was about to fall in Time Square. As we all awaited the New Year tradition I rode Jimmy's hard cock like a professional cowboy, riding a bucking bronco at a rodeo. Rodeo riders want to stay on their animal as long as possible to win. The same is true for me riding a hard dick. I want to make the fuck last and didn't want the boy beneath me to climax prematurely. Early on I had developed a technique whereby I could control matters, delaying my partner's premature ejaculation as well as mine.
I just hated it when a guy would cum as soon as he was inside me, or before. I preferred the man on top position whether I was the fucker or fuckee. The position gave me greater control of the situation; besides, I could watch the facial expression on my partners face. Jimmy smiled up at me from his position lying on his back on the big bed, begging me to ride his rigid rod harder and faster while the others cheered and coaxed us towards climax.
Jimmy's brother and my sister jockeyed for position trying to capture all the intimate details of the action with there hand held video cameras. If I had my way and worked Jimmy just right I wasn't about to let him cum too quickly. I slowed and began riding him in at a more leisurely fashion once again. As the countdown to midnight neared I raised my buttock up slowly to a point where the base of Jimmy's cockhead was resting inside against the inner ring of my anus. As the Waterford Crystal Ball began its slow descent I would ease down Jimmy's six inch steel pole at the same rate mimicking the ball dropping until my bare buttock came to rest on Jimmy's furry pubic bone.
Once the midnight ceremony was concluded I would begin to rise and fall on Jimmy's hard shaft increasing speed until he exploded into the condom he was wearing, filling it with his spunk. After I was done doing Jimmy I would take on the other hand picked young studs again and again for the next few hours, ringing in the New Year. If Jimmy could hold off and not ejaculate prematurely he would be my first fuck for 2006.
The five guys lounging on the king bed waiting their turn to fuck me were self-proclaimed straight boys who were curious. They were young men who led straight lifestyles dating girls, but were curious about same sex sexual unions. All were students who were also athletes. They were positively gorgeous looking male specimens. The two older guys were alumni of our high school who were home on winter break from college. The other three were current students at least juniors at our school. Jimmy, Tommy and my sister had brought us all together in the hotel room for my first of what would become an annual New Year's Eve fuck fest; a fuck fest that would earn me well over six hundred dollars cash money, and signal the beginning of my new career as a male prostitute.
Chapter 2: Earning Big Bucks
The New Year's Eve party 2006 was the beginning for me as a he-whore earning money for my services. I was a fourteen year old high school freshman in 2004 when I first realized my yearning for sex with other boys, and started my apprenticeship towards becoming a male whore. During those novice months prior to the New Year's Eve party I hadn't charged for my services; however, I had come to recognize there was a niche for my new vocation as I was becoming a much sought after male escort. After New Year's Eve party I'd be a bona fide male whore. I had become addicted to anal sex since that first time Jimmy took my cherry as a high school freshman.
From that first time forward I was filled with an uncontrolled lust to be fucked anytime anyplace. I didn't need the money, but I decided that I wouldn't let my body be taken for nothing. When I first started engaging in sex with other boys I was primarily into anal sex for the pure pleasure of it. I soon discovered that the kids I fucked could well afford a fee for my service. No, I was not a cheap slut by any means and didn't fuck just anyone -- I had my rules of engagement.
There was one hard and fast rule: no contact with potential clients by way of the Internet. I didn't get it on with just anyone. Second rule: no older men. I considered anyone over twenty-five to be too old for me. The third rule: clients had to be attractive and healthy in great shape physically with a good-looking cock. I didn't engage in sex with ugly or sickly guys who had fugly looking cocks. I didn't care for really hairy guys either. When it came to clients I was a self-proclaimed cock connoisseur.
No, I didn't fuck every guy who propositioned me, nor would I engage in sex for less than one hundred dollars per session. Some men I charged more, depending upon the time and the set up. Rule four: I wanted to look my clients over before committing to any type sexual encounter, and wanted a total confidentiality agreement. Jimmy and couple of my high school friends were favorites who I did without charge in return for sexual favors. Yes, I was what one might call a finicky fucker -- a cock snob.
Over that first year of high school I developed from a naive freshman into a full fledged male slut. I was pretty much a straightforward stud who enjoyed fucking and sucking; no perverted shit for me, and no S&M. I didn't let guys urinate or defecate on me or in me. I practiced clean and safe sex. I'd quickly learned all the intricacies of anal intercourse during that first year with the help of my sister and friends; moreover, I very much enjoyed the sensual pleasures of getting fucked. So, I decided to capitalize on my talent and the joy thereof.
I didn't let every guy that came along cornhole me. I was choosy about who fucked me, especially when it came to size. I wasn't into pain when it came to sex; therefore, I didn't care to take on guys that were hugely hung. Those guys hung like a horse or mule. Although I preferred to bottom, that is I was the one to get fucked, I would fuck the right guy if there was interest. I broke into the business of engaging in male to male sex accidentally when I started my freshman year in high school after my move to the East Bay with the help of my sister and best friend.
My family which included my older sister moved to our new home in the East Bay during the summer of 2004. My mother had taken a position with University of California, Berkeley while my dad took a new position at a teaching hospital in San Francisco. Prior to moving to Contra Costa County my sister and I had led very sheltered lives. We had both been smothered socially by the home schooling experience, but had excelled academically since we began school. Our education grade point was well above average, but our social lives had been pretty much stunted by our parents control until we moved. Once we moved my sister and I began attending the local high school where our social lives began to blossom and flourish.
Our parents figured that because the area was very upscale there would be little if no chance that we would be exposed to drugs and gangs, so we were allowed to enroll at the local high school. Because of the closeness in our ages Janie and I both started high school at the same time. Most of the students at our high school were children of affluence. Their parents held professional positions in San Francisco and surrounding areas. Many were attorneys, bankers and doctors, while others worked in computer related fields.
With the move to the East Bay my sister and I found our parents gone by early morning everyday throughout the week to catch the BART to work and many times they were late returning home. Both were totally wrapped up in their new jobs which left Janie and me much time to develop outside activities, including sexual exploration. That investigation included canvassing the Internet. We accidentally stumbled across websites devoted to pornography and sex during our leisure after school. We were what society had dubbed as "Latchkey Kids."
Because my sister and I were born prematurely, there was only ten months difference in ages between Janie and me; therefore, due to our ages and the way our birthdays fell we both began high school the same year. To look at us there was no chance mistaking that the two of us were brother and sister. Growing up we had never been shy around each other.
Mother bathed us together until we were about six years of age, so we had seen each other naked many times growing up. Growing up so close we confided in each other about everything, especially our feelings as we entered puberty and developed sexually. We had watched each other develop physically from puberty into adolescence. On occasion we had masturbated together during and after deep philosophical discussions about sex, but I never touched her. We never had sex with each other.
I remember the first time I caught Janie masturbating. A few weeks after we started at our new school we were in my room after school discussing something we had read on a website called Jackinworld. As we conversed about the subject I noticed one of Janie's hands buried inside her cutoffs and the other up inside her blouse. Her hands were moving and she was moaning softly. I asked her what she was doing and she replied that she was sexually stimulating herself, playing with her happy maker. She told me that she could get herself off simply by stimulating her clit. I was curious, so I asked her about her clitoris and to show it to me as I'd yet to be with a girl.
Janie stripped off her clothes as she explained about her love button. She told me that the pleasure nub was a small elongated erectile organ located at the anterior area of the vulva, homologous with the penis. The most sensitive part of a woman's pussy. With her clothes off she spread out on the loveseat across from me, splaying her legs wide displaying the engorged little pink bud at the top of her pussy.
As she traced her fingers around the labia I moved closer to get a better view of what she was doing. Later as I discussed sex with other young men they had no idea what the clitoris was or where it was located. They didn't know that when they gave a woman head that was the part of the pussy that got the attention. A man's tongue or finger tip had to flick the little nub perfectly in order to bring a female recipient to climax.
I soon discovered that most guys didn't know how to give head to another guy or girls when they first began to evolve sexually. I would teach them that the glans, frenulum and area of the circumcision scare were the most sensitive for a guy's cock, and the clit was the area for female stimulation. I also taught them that the area between the scrotal sac and anus was a sensitive area, as well as the asshole itself. Nipples were another area of sensitivity for some guys, not all. Many of my new found sex partners were thankful for my instructions educating them as to the areas of the human body's erogenous zones. I had discovered that there were at least ten zones that would stimulate pleasure in both men and women. Janie helped educate me in the female erogenous zones and I schooled her on the male areas.
Chapter 3: My Sister and I Learned from Each Other
Janie was a very desirous little vixen. I watched as my sister wet her fingers and then traced them around her pink pussy lips. She rubbed and flicked the swollen little red bud with one hand while the other played with her erect nipple: two very sensitive areas of a women's body. As I watched her manipulate her clit and nipple the more she moaned with pleasure; meanwhile, I observed glistening fluid oozing from her pussy. I asked what the substance was, whereby she replied that it was a natural female lubricant, somewhat like my precum. She worked one finger inside her vagina touching her "G" spot while she continued flicking her clit. This technique brought louder moans and groans of pleasure from her; eventually she began crying out, wailing -- ready to climax in a powerful orgasm. Of course, my cock had grown hard by then and needed to breathe watching the erotic show.
Janie noticed from the bulge in my cargos that my cock was in need of attention, so she told me not to be shy to go ahead and whip it out. I unleashed the beast and began flogging it. As I flogged my fully engorged fuck stick Jamie looked upon my trouser snake with fascination. She complimented me on its size and beauty. She was especially intrigued by the beauty of my glans. She told me that I was bigger and had a better looking cockhead than the few boys that she had seen boned up.
As I sat there on the floor beating my meat my ego had just been bolstered. I looked upon my cock with newfound respect. Janie pulled her finger from her pussy, holding it out for me to get a whiff. She told me to lick her finger. I did; it didn't smell or taste that bad. About that time I shot a load of spooge as she exploded in a body shaking wild orgasm. We came down from our sexual highs and then she asked me if I'd scored with a girl since we started school. I told her no, that I was curious about sex with guys and what I really wanted was to have sex with a guy. Of course, I reinforced quickly that I wasn't gay, I was just curious.
My older sister smiled at me and said she might be able to help me out with my curiosity. She told me that she'd been hanging out with a junior named Tommy Connor. She said that Tommy had told her that his younger brother who was a freshman might be bisexual, and that he was looking for a male partner with whom to experiment. She asked me why I wanted to do it with a guy. I told her that I'd seen guys on the Internet engaging in sex oral and anal sex. I said that watching guys suck each other or take it up the butt had definitely peaked my curiosity. I told her that I'd been finger fucking myself for a while and that it felt totally awesome. She asked me if I'd done anything with a guy yet. To which I replied no.
I asked my sister if she had fucked or sucked Tommy yet to which she replied no, but she said that she wanted to do him soon. She told me that she had masturbated him on couple of occasions, but that was it. I was curious, so I questioned her about how big he was to which she replied about seven maybe eight inches and fat. I was curious whether size played a part in her decision no to perform oral sex on Tommy. She said that the only thing that put her off about giving Tommy a blowjob was that he wasn't circumcised.
Janie told me that she had discussed oral sex and uncut guys with her girlfriends at school and discovered that most of them preferred not to perform oral sex on the uncircumcised guys. She said it had to do with the aroma and cleanliness of uncut guys. Janie also said that her and her girl friends found cut guy's cocks much more pleasing to look at than uncut guys, especially in the flaccid state. She told me that the girls had unflattering nicknames for guys that were uncircumcised.
One of the things I'd discovered on the Internet was that circumcision was a very controversial subject. Some guys were adamant about retaining their foreskin, while others were upset that their parents didn't have them cut at birth. I was convinced that circumcision would be a heated debate that could probably go on for centuries to come. Janie warned me again to be extremely careful. To make sure my partners were health and clean, but most of all wear a condom if and when I engaged in anal sex with a guy. She also suggested that I go online to research the subject. I told her I'd found a couple of different websites that explained in great detail the ins and outs of anal sex.
The websites I'd reviewed gave detailed descriptions about how to prepare prior to engaging in anal sex. The websites described different positions and techniques as well as preparatory procedures. I told Janie that I'd read about anilingus and rim jobs online and wanted to try that too. Once again, she warned me to be very careful and use a condom when engaging in any type anal sex. Before we broke off our conversation that day Janie told me that she'd mention to Tommy that I may want to hook up with his younger brother to experiment sexually.
Chapter 4: Meeting Jimmy
A few days later Tommy's younger brother Jimmy contacted me after wrestling practice wanting to know more about getting together. We met a couple of more times after wrestling, feeling each other out. He came over to my house where we browsed the Internet looking for information about gay male sex before we made a date. Jimmy said when we got together that I wasn't to tell anyone. I agreed and asked that he not tell anyone either. Two weeks before my date with Jimmy, Janie presented me with a phallic replica butt plug she'd bought on line. The little plug was about four inches long by four inches in girth with a nice looking cock head on it. She also had gotten me a box of condoms and some Astroglide lubricant. During the next few days I began experimenting with the phallic butt plug.
I used it trying to loosen my asshole up so I'd be ready the first time Jimmy entered me. I would lube up my ass and the anal toy before inserting it. I would place the plug in my ass of a night and then leave it in place until the next morning. Inserting the butt plug was a painful experience the first few times; however, after about a half dozen times I had gotten used to it. The plug was just the right length to rub against my prostate. I would twist and turn in bed, bringing great pleasure to me throughout the night. I learned how to expand and contract my sphincter pushing out like I was getting ready for a bowel movement to make entry easier.
As I lubricated the toy and prepared to insert it I spread my butt cheeks opening my asshole for inspection. I used one of Janie's hand held mirror to watch my bottom as I squirted the Astroglide into my anal opening. Then I would place the head of the toy at the entrance, tensing up my sphincter muscle and then loosening it. As I performed the exercise I would insert more of the phallic toy into the hole watching my asshole gobble up the intruding cockhead sucking it past both rings into my anal cavity. There was a flare at the base so as to not let the device go all the way inside me.
With each exercise the entry process became more bearable, but still there was a certain amount of pain associated with it. A week after the first phallic present Janie gifted me with a dildo that was equipped with a suction cup at the base: a five inch by five inch model. When I took my shower I would attach the suction cup to the shower surround and then I would begin fucking it with my soapy asshole while I showered. What an incredibly awesome feeling.
Finally, the day arrived for the big date where Jimmy and I planned to spend the weekend together holed up at his house. After school on Friday we rode home with his older brother. Once we got to the Connor home Jimmy showed me around. The first order of business was to stow my backpack in his room and then eat dinner with Jimmy and his family before his mom and dad left for Lake Tahoe.
Friday 2004 was New Year's Eve, so Jimmy's parents were heading off to Lake Tahoe for a weekend of fun. Tommy was going skiing and snow boarding with his friends for the weekend, so by ten that night Jimmy and I were alone to begin our weekend of fun, a night of sex. For us the weekend would be a cram course in sex. We went to his bedroom where we got naked and sat cross legged across from each other on his big bed to discuss things.
I told Jimmy that the first thing we should do was go take a shower. I assured my friend that showering was an integral part of foreplay; it was also to cleanse our bodies, especially our asses internally and externally. Once we got to the bathroom and into the shower I guided the neophyte through all prep that I wanted us to do before we got down to having sex. In the shower I prepared Jimmy for our first sexual union.
As I stood behind Jimmy with my semi erect cock resting at his ass crack I explained to him about my expectations for the night. I told him that I planned to perform anilingus on him as while I played with his erect nipples. I thought the boy was going to ejaculate before we got out of the shower. I learned my first lesson in the shower: don't play with Jimmy's nipples unless I wanted a sticky mess to cleanup. I also told Jimmy that if he didn't want to reciprocate that was fine with me, but I did want him to fuck me at least once, maybe more before our date was over.
Once out of the shower and back in the bedroom we began touching each other tenderly, stroking each other's bodies in a sensual manner, tantalizing our hard cocks. Jimmy, like his older brother wasn't circumcised, but he had a great looking cock that appeared to be about six inches long and maybe about four and half to five inches thick, mine was a little bigger.
Jimmy was quite taken by my uncircumcised cock, especially the glans. As he played with me he asked if I would let him suck my cock. I agreed. Jimmy got between my legs where he prepared to take my cock orally. I found that due to his lack of experience I had to guide him for as few minutes, but then he had the process down pat. I found out over the years that guys have a natural ability, instinct if you will, for sucking cock. After few minutes he asked me if I wanted to suck him. I told him that I was more interested in having him cornhole me rather than sucking his dick.
I told Jimmy that I wanted to give him a rim job before he fucked me. He had no idea what I was talking about, but after a brief explanation he was all for it. He lay back on his big bed while I put a pillow under his buttock before getting between his legs. I ordered him to grab his legs, pulling them back against his chest. Once his legs were pulled back I asked that he reach down and spread his buttock apart. His crotch area still smelled fresh of Irish Spring body wash and his hairless ass crack had not a blemish. I handed Jimmy the hand held mirror so he could get a good look at his open pink asshole. I held his ass cheeks apart so he might get a better look. I blew my warm breath softly on his pink pucker.
Jimmy shuddered sucking in a breath. His asshole closed down at the same time. He exclaimed that watching his asshole was totally awesome. I asked him if he had ever finger fuck himself. To which he relied no. I told him to watch me as I began tonguing his asshole. He wailed loudly as my tongue touched his pink sphincter as his body convulsed and trembled. After a few minutes I came up for air and Jimmy told me that he had never experienced anything like that in his life. I told him there was more to come, but I need for him to fill my ass with his dick. As I repositioned on the bed Jimmy told me that I had one of the most beautiful looking cockhead he'd ever seen.
My young sex partner inflated my ego telling me that my glans was a thing of beauty. From what I'd read on line Jimmy was endowed with a pretty average size male penis and was among roughly a third of the male population in the United States that wasn't circumcised. Before I prepared to get fuck Jimmy wanted to suck my cock again. After a short while of him nibbling on my knob I suggested we stop and get ready for him to cornhole me. I started pulling items from my backpack displaying them on the bed.
I pulled the box of condoms and bottle of Astroglide from my backpack that Janie had gotten for me. Jimmy remarked that I'd come well prepared. He listened in amazement as I choreographed the details about our first sexual encounter was to go. I also showed Jimmy my two dildos and explained how and what I used them for. He was surprised as he'd never seen a dildo before. He told me that I knew a whole lot more about sex than he did and wanted to know how I knew so much. I explained that Janie and I browsed the Internet regularly. He told me that jacking off and a few sixty-nine sessions with his best buds was as far as he'd gone, but he said that he was ready to try new stuff. He was curious and definitely wanted to experience fucking me.