Sexy 14-year-old Penny comes up with a clever way to make $1,000. She organizes a raffle at her middle school where the prize is a carnal romp with her!
Part One
Of course, as a male I wasn’t there in the eighth-grade girls’ health class that Wednesday afternoon when Penelope (Penny) Davidson came up with the idea for the sex raffle, but this is what we horny boys at Laurel Street Middle School all heard later on.
During that class, the teacher, Mrs. Bentley, was trying to give the 30 girls a lesson about morality which led to a discussion about prostitution. At age 14, Penny was easily the most sexually attractive female in the school. She had a build that was the envy of most high school girls. She was also very pretty, with a cute face and a lovely head of curly auburn hair. Rumor had it that Penny was sexually active with a 17-year-old high school boyfriend. (As my classmate Freddy Miller put it, “Penny Davidson is the total package.”) She was also a fairly decent and inquisitive student, too. Penny questioned Mrs. Bentley about why a girl shouldn’t engage in prostitution as a form of employment if she so desired. Penny asked aloud, “If a girl is an excellent typist, no one would stop her from using that talent and getting paid for it. The same idea applies if she is a good hairstylist. So, if she’s good at sex, and males are willing to pay for it, why shouldn’t a girl be allowed to offer sexual services for pay and reap the rewards?”
Mrs. Bentley was probably pushing 60 and had been teaching at LSMS since 1947. This was May 1978. Times were definitely changing because she had never heard such a steamy, forthright inquiry in all the years she had taught girls’ health classes. Moreover, Penny had phrased her question in such a logical way that Mrs. Bentley had difficulty coming up with a good rebuttal answer.
Penny, aware she was winning the argument, added the bold statement that she could probably make $1,000 in less than a week if she conducted a sex lottery with herself as the prize, selling chances at $1 apiece to all the boys in the school whom she figured would like to bed her. Mrs. Bentley was horrified at the whole idea, but she couldn’t successfully refute what Penny was saying. By the time the class ended, Penny said she was going to do just that. Apparently, about a quarter of the girls in the health class cheered Penny for being an independent thinker, but the majority were just as shocked as their teacher was.
That class took place just before lunch. By the time lunch period had ended, word of Penny’s raffle had spread like wildfire through every classroom. The boys, with few exceptions, thought it was a marvelous idea and were figuring out how many tickets they could afford to purchase. I, Douglas Morgan, was definitely going to buy at least five chances. I had often fantasized about drilling the luscious Penny Davidson since I saw her on the first day of classes in the seventh grade. I wasn’t close to being in Penny’s league in looks and popularity, so I concluded this lottery was my best chance to make my dream a reality. Heck, it was my only chance. Despite my odds of winning being long, I figured it was money well spent.
When she was asked about the raffle, Penny proved she was completely serious. By the next day, she had created a thick list comprised of two dozen sheets of lined paper. On the lines were all the numbers from one to one thousand. If you bought a chance to copulate with Penny, you paid her a dollar, selected a number that had not yet been chosen, and wrote your name on that line. That was the equivalent of your ticket. Penny said she’d already created small lots, each bearing one of those thousand numbers. Once every line had been sold, those thousand lots would be put into some sort of large drum. Penny would hold a public drawing to randomly select a number, and some lucky boy would be very happy.
I was like Penny in that I had come up with a way to earn money from my fellow students. Unlike Penny, mine didn’t involve anything sexual. As an excellent speller and grammarian, it was known that I would proofread students’ essays for the princely sum of 25 cents so they wouldn’t be penalized by their English teachers for such avoidable errors. I typically made about $2 per week doing that task. That week I put that money towards Penny’s raffle and took another $3 from my petty cash box that I kept for special occasions. I figured Penny’s sex lottery definitely qualified.
Some teachers heard about Penny’s idea. They could criticize her and advise her not to do it, but they really could not stop Penny from organizing her raffle as long as she sold her chances quietly and her sex act with the winner wasn’t done on school property. My home room teacher, Mr. Easterbrook, a gregarious bachelor in his fifties, quietly told me he would have purchased $10 worth of chances himself “to screw that sexpot I see every day,” but that would certainly cost him his job. He further said he envied whomever the lucky winner might be.
In less than a week, Penny had indeed sold $1,000 worth of chances, proving that her estimate was quite accurate. (She later lamented not trying to sell twice as many chances to double her profit.) Penny informed anyone who was interested that she’d conduct the drawing the following afternoon once school had been dismissed. The time would be 4 p.m. and the site would be a small park located about a block east of the school. I estimate 250 anxious boys showed up with their fingers crossed. I was one of them.
With my $5, I had bought lines 87, 112, 358, 402, and 438. They were basically random picks, except for #438. That had been the answer to a math problem I had solved to complete my homework on Monday, so I figured maybe it was a sign from above to choose that particular number.
At the appointed time, and with a huge audience watching her, Penny thanked everyone who bought chances. She said she had no idea how she was going to spend the $1,000, but she cavalierly stated it “would be on something totally frivolous”. I couldn’t help but notice that Penny was wearing an especially tight-fitting yellow blouse that afternoon, presumably to highlight what the lottery prize was. With great fanfare, Penny dumped the thousand numbered lots into what looked like a pink clothes hamper. She agitated and stirred the lots with her right arm until they were thoroughly mixed. Everyone became silent for a few moments as the critical moment drew near. With her eyes closed, Penny returned her right arm inside the receptacle and pulled out a folded lot. She opened it. “The winning number is 438,” she announced.
I let out a loud and excited yelp, as I immediately recognized that 438 was one of my five numbers! Penny diligently checked it against her list of names to confirm I had won the jackpot. “The winner,” she declared with a warm smile, “is Douglas Morgan…whoever that is.”
She’d know me soon enough.
Part Two
Most of the losers accepted the result well. Some even congratulated me on my good fortune or patted me on the back. However, one miffed classmate, Brian Zimmerman, whom I disliked and vice versa, muttered, “Lucky fucker!” and stormed off angrily. He was right on both counts: I had been extremely lucky having had just a 1/200 chance of winning with my five lots—and, for the first time in my life, I was going to be a fucker!
Penny Davidson didn’t know who I was by name, but when I approached her and said I was the lottery winner, recognition began to set in. I was prepared to show her ID from my wallet in case it was required. “Oh! I know you, Douglas!” she declared. “I recognize you. You are in Mr. Easterbrook’s homeroom. You’re the guy who does proofreading for a quarter. I hear you’re a super nice guy. It’s great that you won! I could have ended up with a winner who was horrible.”
I took not being horrible as a compliment, as I was sure it was intended. I was far more complimentary toward her, telling Penny that she was a stunningly gorgeous girl who could have easily sold 5,000 tickets for her raffle if she really tried. Normally I wouldn’t have had the nerve to talk to any of the truly beautiful girls at my school but knowing that I was soon going to screw Penny’s brains out made having a conversation with her seem quite ordinary.
“I guess we need to set a date, a time and a place for our fuck, don’t we, Douglas?” Penny stated.
“Yeah, I think that’s necessary,” I added with a smile. “I’ll show up anytime and anyplace.” My eagerness for this to happen was obvious.
“How about tomorrow at about this time?” Penny suggested. “There’s an apartment building about two blocks from here. I don’t live there, but my high school boyfriend Greg does. It has a community room in the basement that is hardly ever used. It’s got a big, comfortable couch we could use. Greg and I fuck on it all the time.”
“Won’t Greg object to you having sex with me?” I asked with a concerned tone in my voice.
“No, not at all,” was Penny’s surprise reply. “We don’t have a typical boyfriend/girlfriend relationship. We only get together to screw because we both enjoy it. I just refer to Greg as my boyfriend because I can’t think of a better term to use.”
“Oh!” I said because I could think of nothing better to say. Then I asked, “Did Greg even know about your lottery?”
“Yeah, I told him all about it,” Penny said. “He thought it was a very creative way for me to collect $1,000. In fact, he bought three chances for himself to show he supported my idea.”
Penny and I arranged to meet immediately after school the next day at the same park where the lottery drawing had taken place. Then we’d walk together to Greg’s apartment building. I got little sleep overnight. I couldn’t wait to shove my hard dick into the most desirable girl at my school. My attention span in class the next day was close to zero as thoughts of sex drove everything else out of my mind from the time the opening announcements were read until the dismissal bell six hours later. I noticed I had a persistent erection while seated at my desk just from constantly imagining what screwing Penny would be like. This was only slightly out of the ordinary for a 14-year-old boy, I suppose. Uncontrollable erections were commonplace for that demographic.
I hadn’t told anyone that this was the big day, but Penny must have, because just after the final bell rang, I had two classmates wish me luck on my carnal adventure. “Give Penny a good blast of cum for me, Douglas!” said one of them. It was Jimmy Cooper who had been a school chum of mine since kindergarten. “I blew $8 on raffle chances, but if I couldn’t be the winner, I’m glad it was someone like you. Now run off! Don’t keep that beautiful, sexy girl waiting!”
Part Three
Such was my high level of anticipation that I almost sprinted to the park. I got there ahead of Penny. As I waited for her arrival, squirming on a bench, the horrible possibility ran through my mind that Penny may have orchestrated a gigantic con on the entire male population of our school to bilk them out of $1,000. That turned out to be an unnecessary worry. About a minute later, Penny showed up with a smile on her face. She greeted me with a lovely, sincere hug—the first physical contact we’d ever had. It felt wonderful. I thought to myself if a simple embrace from this sexpot was so terrific, imagine what sexual intercourse with Penny was going to be like!
We merrily chatted about school stuff—homework, an upcoming field trip to a science museum, and other bits of esoterica—as we walked the short distance to Greg’s apartment. No one needed to grant us entry. The two of us just walked right in, made a right turn, and descended a staircase one floor to the basement where the large community room was located. “I hope no one is using the room now,” Penny said.
That thought jolted me. The one thing I did not want was a last-minute postponement because people were playing table tennis or watching a soap opera in the same room where Penny and I intended to screw. The door was closed but unlocked. Penny knocked on it twice without getting a response, so she let us in. She flicked on the light switch—and locked the door behind us. Penny had obviously done this with Greg on numerous occasions.
There were indeed a color television set and a ping-pong table in the large room, but no one was using either at the moment—thank heavens! Penny led me to the couch but stopped about two feet in front of it. “I figure you are the romantic type, Douglas, so let’s do some kissing before we start our fucking. Is that okay with you?”
As someone with almost zero experience with sex or romance, I didn’t know how to respond, so I shrugged my shoulders and said, “I guess so.” Penny, at about 5’6”, was only about half an inch shorter than I was. She gave me a fabulous romantic kiss, which was itself worth the $5 I had spent on lottery chances.
We moved our kissing to the soft couch. I was eager to begin the good stuff, of course, but I dared not be the instigator. Penny took care of that by removing the expensive sweater and unbuttoning the shirt I was wearing. (I had made a point of dressing up for school that day—which seemed a highly suspicious act to my mother. “Trying to impress a girl, Douglas?” she curiously asked me. As I left the house, I told her she was in the right ballpark, but I didn’t care to elaborate further.)
Penny gave me a naughty grin and said, “You can unbutton my blouse, if you would like to do that, Douglas.”
“Yes, I think I would!” I told her. I rushed through it. Her mauve garment was on the floor within about ten seconds. She was wearing a very sexy white bra that lifted her treasures temptingly—not that I needed to be aroused at that point. I had been constantly aroused on some level since lot #438 had been drawn 24 hours earlier. I didn’t really know how to unclasp a brassiere, so I let Penny take care of that minor chore. Seconds later her wonderful, big tits were bouncing in my face. I immediately cupped them in my hands and started to lick and suck on them.
Penny stated the obvious. “I see you like my boobs!”
“Every normal boy at our school loves your boobs, Penny—but I’m the guy who is caressing them at the moment.” After about half a minute of sensual licks, sucks, and gropes, Penny stood up so she could get rid of her slacks, socks and underwear. I did the same. I was bold enough to help Penny shed her panties, which, I noticed, were the same color as her blouse. Why any girl would worry about making sure her blouse and panties were a matching shade was a mystery to me.
I became fixated on Penny’s vagina, which was a bit hairier than I had expected. We sat back down on the couch and I began to fondle her private part with slow, gentle strokes from my right hand. Penny noted, “You have a delicate touch, Douglas. I like that about you.”
Penny began to stroke my penis which was already fully erect. “Firm, straight and tall!” Penny happily declared. “Hey, what more can a girl ask for?” That comment gave my ego a boost. Not long afterwards Penny said. “It’s a real beauty; I have to suck on it.”
Of course, I had no objection to that plan of Penny’s. I leaned backwards and gave my lover full access to my rod. It crossed my mind that Greg had to be the luckiest guy on the planet to have Penny perform this sex act on him regularly. She was clearly experienced at this as she massaged my balls, stroked my shaft upward, and licked on its head—all simultaneously.
“Like what I’m doing to you, Douglas?” Penny asked me sweetly.
I quickly replied, “It would be impossible to dislike this, Penny. You are amazing!”
Penny stopped her excellent licking long enough to make the following suggestion: “Why don’t I just ride your dick until you ejaculate?” Being a compliant fellow, I said that would be delightful. (Actually, I shouted, “Hell yeah!”) For comfort and mobility, Penny said we ought to do this while I was seated on the footstool in front of the couch. “Greg and I fuck this way all the time; it’s great,” she informed me
.
I took a seat on the stool while Penny took a seat on my lap. We had another long romantic kiss, after which Penny said she was really enjoying being intimate with me. She also added that she felt like she had stolen the $1,000 she had collected from the lottery players. I laughed. Penny then positioned herself to drop her vagina onto my penis. As Penny lowered her body onto mine, the sensation was heavenly. There was no better way of describing it. Every fraction of an inch she slid down my rod was exponentially more pleasurable than the previous one. Penny’s pussy wasn’t especially tight—or my manhood wasn’t especially thick—because she had little trouble making me go balls deep inside her. I moaned in ecstasy.
“Do you like what you won yesterday, Douglas? I know I’m enjoying it,” she commented, not really expecting a response from me.
I managed to utter, “It’s bloody fantastic!” as I repeatedly lifted my human lottery prize up and down my shaft.
Then Penny gave me some information I hadn’t even thought about—but certainly should have. “Feel free to blow your load inside me, Douglas. I took a pill, so you have absolutely nothing to worry about. I’m sure you want to do that, right? Greg always comes inside me—unless he has a premature ejaculation—which happens occasionally.”
“I don’t doubt that!” I commented. “I nearly came in my pants five seconds after you picked lot #438 yesterday afternoon!”
Penny laughed loudly, saying that was one of the greatest compliments she had ever been given. She gave me another long kiss. In the middle of it, I launched a huge load of warm semen into her vagina. It was the best feeling in my life to that point. It’s been nearly half a century since that cum shot exploded from my dick. Few feelings have surpassed or even equaled it.
We stayed conjoined for quite a long time, my throbbing rod impaled within Penny’s pussy until its stiffness vanished. Then I pulled out. Penny was in no hurry to end our sexual romp, which I found very flattering. I lovingly caressed her body from head to toe for another half hour. Of course, I spent plenty of that time handling Penny’s best features and telling her how sensational they were.
“Douglas, you are actually quite good at sex and lovemaking in general,” Penny kindly told me. “Maybe you should conduct a lottery of your own for the benefit of all the girls at our school. If you do, you can count on me to buy at least $5 worth of tickets.”
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