Stewart's Gambling Debt

When a high school gambler falls into debt betting on football games, he coerces his promiscuous, 18-year-old stepsister to help pay it off with sexual favors.

[Author's note: This story previously appeared on this website. it was expunged in May because of the new age requirement for characters. These necessary edits have been made.]

Part One

Stewart Ketchum was never exactly a friend of mine; he was a high school acquaintance at best. We both liked to bet on sports because we both thought we knew a lot about the subject. We were both 16 years old when we started wagering with each other for minuscule amounts. However, it was in the autumn of 1990, at age 18, when Stewart ran into a streak of bad luck betting on football—and I was the beneficiary of it.

During the NCAA football season that year, Stewart and I (Frankie Callini) began regularly betting on various games with each other. They were simple win/loss bets; no point spreads were factored into any of our wagers. We’d find a handful of collegiate games prior to each Saturday where we disagreed on which team would win and put $5 per game on it—a substantial amount for teenagers to be wagering in those days. That first weekend we bet on eight games. I won seven and lost just one. That meant I was up $30, which I thought was a terrific amount of money. However, it turned out to be more than that. It became a valuable nest egg! I learned very quickly that Stewart didn’t like to lose when he gambled...and he’d try to get even as quickly as possible with large wagers.

It was also the opening weekend for professional football. Instead of paying his debt immediately from the college games that he’d lost, Stewart wanted a chance to get even with me with a $30 wager on a single NFL game. Stewart took the Denver Broncos, I took the Los Angeles Raiders, double or nothing, on the $30 he already owed me. The Raiders won by a 14-9 score. Now he owed me $60. Stewart asked if I would just run a tab on his losses. I said yes, but it was on the understanding that I could stop the tab at any time and demand full payment on whatever debt had accrued. He agreed to that important condition.

The following Saturday we made another double-or-nothing bet on college football. He took Michigan while I backed Notre Dame. My team won, 24-23. Now I was up $120, and Stewart was becoming angry over losing close games—and a lot of money to me. He called me that night to ask if we’d make another bet for his full debt on an NFL game the next day. I was obviously on a hot streak, so I agreed despite the risk. He took the hometown Green Bay Packers while I backed the visiting Chicago Bears. Chicago won in a cakewalk, 31-13. Stewart’s debt to me had now risen to a remarkable total of $240.

Before that lopsided game had even ended, Stewart phoned me to concede defeat, and to plead for one more double-or-nothing bet on the Monday night game the following evening to try to reduce his debt to me to zero. This time I took the Denver Broncos against the Kansas City Chiefs. Denver won 24-23—the same score of the Notre Dame-Michigan game two days earlier. Amazingly, I was now up $480 after just a couple of weekends. That night, once the game had ended around midnight, I phoned Stewart to say that I feared my good fortune could not last indefinitely...so I wanted to be paid. He said he’d talk to me at school the next morning about how he was going to settle his debt to me.

“There’s nothing much to discuss,” I insisted brusquely. “You owe me $480...and I prefer cash. I’ll see you at school tomorrow.”

Stewart found me at my locker about five minutes before classes began. He handed me a bulky envelope that contained $338 in banknotes. This meant he was short by exactly $142. I assumed he had likely scraped every possible source for money he could find because much of it was in small denominations. I was not pleased with the insufficient amount he had given me.

“Welching on a bet is a great way to ruin your good name,” I advised Stewart. “If you don’t find a way to pay me the full amount you owe by tomorrow, I’ll make it well known that your word is worthless.” It was a threat that I meant sincerely. Stewart said he’d do his best to make up the shortfall.

The next day Stewart failed to meet his total obligation. He handed me just $31 in crumpled bills. After that payment, he was still $111 in debt to me. Again, I wasn’t happy with Stewart not paying his debt to me in full.

I said sternly, “This won’t do, Stewart, and you know it.”

“Yeah, I know,” he said, “but I have something you might want in lieu of that $111 I still owe you.” He paused for a moment and suggested, “How about my stepsister, Suzanne?”

I naively did not immediately know what he meant, so Stewart freely elaborated. “Come by my house this Saturday night. My parents are away for the whole weekend. You can fuck Suzanne literally all night. That ought to be worth $111.”

My mind started to picture this unorthodox form of payment, and I must admit I was very intrigued by the sexy and unexpected offer. However, I had plenty of questions for Stewart before I’d even begin to consider accepting his unusual deal.

“I don’t even know your stepsister,” I informed him. “Does she go to this school?”

“Yes, but she doesn't have the same last name as I do. She's Suzanne Murphy. She is 18, the same age we are."

That name rang a bell, but just barely. I think she had been in one or two of my classes. I couldn't really picture her, however.

“What makes you think she’ll agree to have sex with me to get you out of paying me $111?” I asked Stewart. It seemed to be a sensible question.

“She’s got no choice; I have something on her, ” Stewart explained. “I caught her drinking and smoking marijuana with a few of her friends back in August. I told Suzanne I wouldn't fink on her to our mom and dad, but she’d have to owe me a big favor in return. Well, this can be the favor...if you’ll accept a night in the sack with her to wipe out my debt to you.”

I was still trying to process this utterly wild offer in my mind. “So, you honestly think she’d agree to do this for you?” I inquired.

“She already has!” Stewart announced. “I asked her last night when I knew I was going to lose our latest football wager two nights ago. She wants to get even with me, so she told me that she would be your bedmate this Saturday as the favor she owes to me. Honestly, Frankie, she really didn’t think too much about it. Suzanne enjoys having sex, so this isn’t really a big deal for her.”

I was a little bit shocked by what Stewart had just said. “So, you’re telling me that Suzanne frequently sleeps around?” I asked.

“Yes, she does, ” Stewart bluntly confided to me. Then his voice dropped to nearly a whisper when he said, “Nobody besides Suzanne and I know this, but not long after my dad married Suzanne’s mom two years ago, the two of us started fucking. She was the one who instigated it! Of course I enjoyed banging her too! Suzanne really is a good fuck—and she has a nice body. Here, I’ll show you, Frankie. Take a look for yourself.”

Stewart produced two photos of his stepsister for me to examine. In the first one, Suzanne was dressed in loose summer clothing: Shorts, sandals, an oversize yellow t-shirt, and a Gilligan-type cloth hat. That wardrobe disguised her womanly assets, so it wasn't a great advertisement of her charms. Nevertheless, I politely commented, “She’s a real cutie.”

“Yes, she is, ” agreed Stewart. “That photo was taken a couple of years ago when Suzanne was 16. Here’s another one I took just last week when she was coming out of the shower.”

This snapshot left nothing to the imagination. It was a frontal view of the nude, smiling Suzanne. She had a lovely set of perky breasts that definitely caught my attention. Her brunette hair looked to be slightly longer and curlier, too. Suzanne also had a small patch of pubic hair on her vagina which she was fingering. I knew she wasn’t just “coming out of the shower,” as Stewart had claimed. Suzanne had obviously posed for her stepbrother and sex partner.

Now I was definitely interested in Stewart’s offer. Certainly, my having another $111 in cash would be nice, but my recent good fortune from betting on football and winning meant it was basically found money. However, I figured my getting to fuck a pretty and desirable sexpot like Suzanne Murphy—for hours on end—was worth deducting less than a quarter of my $480 windfall.

“Okay, Stewart, it’s a deal.” I announced. “I get Suzanne for all of Saturday night and your debt to me is wiped out. I’ll tell my parents that you’ve invited me to stay the night to watch and discuss sports. They won’t question my story.”

“I think we have a deal!” Stewart happily stated. He shook my hand in a businesslike manner and walked off to his home room. Stewart didn’t seem bothered in the slightest that he had, in effect, prostituted his teenage stepsister. After considering everything, I knew two things were certain: Saturday was going to be a memorable night for me, and Stewart Ketchum was a genuinely sleazy guy.

Part Two

When Saturday morning came, I phoned Stewart to confirm that every part of the plan was still in place for that evening. He assured me it was. I told him I’d show up at his house around 6:30 p.m. We would order pizza (my treat) for me, him, and Suzanne as our evening meal.

I packed an overnight bag with a change of clothing, a pair of pajamas (which I hoped I would not wear), and an already-opened box of contraceptives that I had bought six months before when I had a promiscuous, short-term girlfriend named Cheryl. (I really didn’t want to be wearing one of those, either!) Before I left on foot for the Ketchum house, which was located about six blocks from mine, I stopped at a chocolatier to purchase a large box of sweets as a gift for Suzanne. I didn’t want my bedmate to think I was as much of a creep as her stepbrother clearly was.

Stewart opened the door when I arrived. As we had never met before, he introduced me to Suzanne, who was standing nearby in the family kitchen. She was slightly shorter than I expected. More importantly, she was prettier in person than she was in the two photographs I had seen of her. Suzanne was greatly pleased with the box of chocolates I had brought for her as a gift. She flashed a very appealing smile at me.

“What a nice surprise! You are a great guy, Frankie!” she exclaimed and gave me a quick hug. Then she felt compelled to add, “You’re going to get a great fuck from me tonight.”

It seemed shocking to hear those words come from the mouth of a girl just moments after I had met her, but I got used to Suzanne’s startling openness very quickly. Once the pizza arrived and we began to chat, Suzanne happily talked about various sexual things. Clearly, she had no moral regrets about what was going to happen soon. Such topics as her favorite coital positions and the names and attributes of a few boys she had screwed in the past few years certainly kept the conversation quite lively and very interesting.

When the last slice of pizza had been eaten, Stewart took the empty box and plates to the kitchen where the latter would be washed. Stewart then announced he had considered asking our permission for him to watch our night of fucking, but he determined that might be “slightly awkward,” so he had changed his mind about it not long after I had arrived. Suzanne and I made no remarks, but I was beginning to hold Stewart in very low esteem. That was not going to stop me from getting my $111 worth of sex from his cute, promiscuous stepsister, however!

Suzanne, just out of curiosity, wanted to know how old I was when I first had sex..

“Fourteen,” I replied. “Dorothy Miller, a classmate who was 13, and I had an impromptu make-out session that got a little bit out of control one afternoon after school had ended. Let’s just say it didn’t last too long and it was very messy.”

Suzanne laughed and commented in an experienced way, “Let’s hope you do better tonight, Frankie.” Both Stewart and I laughed at Suzanne’s expertise on such things. He was still chuckling when he headed to the kitchen to begin washing the dirty dishes.

“I guess I’ll see you two in the morning, ” he noted. Stewart’s parting words were cheery ones: “Give him a good fucking, Suzanne...and give her a good fucking, Frankie. Good night to both of you.”

Part Three

Suzanne took my hand and led me into her bedroom at the end of a long, carpeted hallway. It was exactly how I pictured an 18-year-old girl’s bedroom would be decorated. The color scheme was an attractive mixture of pink and baby blue. On the walls were posters of some teenage singers and celebrities I didn’t recognize. (I wasn’t much into pop culture.) Her bed had a few stuffed animals strewn upon it—which was kind of sexy to me. They gave off an air of innocence that Suzanne clearly did not possess. We both gathered up the soft little creatures and gently placed them in a distant corner of the room. Suzanne seemed eager to get down to business as she immediately began to pull down the bedspread and sheets. I stopped her by saying, “Hey, what’s the rush, Suzanne? How about a bit of foreplay to get us warmed up, sweetheart? We have a long night of sex ahead of us. Let’s enjoy every minute of it!”

I could tell by the confused look on Suzanne’s face that she was surprisingly unfamiliar with the term “foreplay,” so I had to provide her with some examples. I said, “You know...hugging, kissing, feeling, fondling, caressing, licking, sucking...all those fun things we can do before we actually start fucking.”

Suzanne surprised me by replying, “Frankie, no boy I’ve ever had sex with has ever wanted to do that! It’s always been we get undressed quickly and he shoves his dick inside me right away without any delay. You are a special guy.”

After hearing that kind statement, I truly felt sorry for her. I said, “Come here, Suzanne,” and motioned for her to sit beside me on the edge of her bed, which she promptly did. I put my right arm around her and commented, “It sounds like you’ve been deprived of a lot of fun in your sex life. I’ll tell you what I’ll do: I’m still going to fuck you—that’s a given—but I’m going to make love to you as romantically as possible beforehand. I think you’ll like that. Making love to a beautiful girl—and that’s what you are—will be a real pleasure for me. How does that sound, honey?”

A very happy and contented expression came over Suzanne’s face. “Wow, Frankie, that sounds great...terrific...wonderful!” she said. “I knew you were a different type of boy when you showed up here with that lovely box of chocolates for me. Okay, let’s do it. Tell me what to do.”

“You won’t have to do very much at all, Suzanne, ” I happily informed her. “I’ll mostly be the giver and you’ll mostly be the receiver. I’m going to start by undressing you.” Thus, my sexual encounter with 18-year-old Suzanne Murphy, the petite stepsister of a sleazy debtor, began with a hint of love in the air.

Suzanne was wearing a tight-fitting, brown top, similar to a tennis shirt. I undid the four buttons it had and lifted it off her torso. Her white brassiere was revealed. It supported her luscious breasts that were above average in size for a high school girl. She was about to take it off when I stopped her.

“No, no, Suzanne,” I said softly. “I’ll do all the work! Let me have the fun of removing every stitch of clothing from your sexy body.” She nodded without speaking and flashed me a warm smile.

I was about to continue with my enjoyable task when Suzanne said, “Hey, at least allow me to take off my shoes!” I laughed and told her that was okay with me. She removed her white and pink sneakers and gently put them under the bed.

“You can unbutton your jeans for me, too, Suzanne, ” I instructed her. She did and I pulled them off her legs. She was wearing cute white panties with a red border and a Minnie Mouse design on them. For some reason, I found that youthful detail to be very sexy indeed! She also had on a pair of gray socks—the small kind the just came to her ankles. I took those off her feet and noticed she had pretty little toes—a subtle, physical trait that a lot of girls do not possess. I paused before I went any further. “Just stand up for a moment, Suzanne. I just want to enjoy the lovely sight of you in your underwear before I do anything else,” I told her. “My goodness, you are truly an adorable girl. What a turn-on you are!”

I felt my erection starting to slowly build, but I opted to keep my briefs on as I removed the rest of my clothing and cavalierly tossed it all near the stuffed animals in the corner of the bedroom. I got onto the bed beside Suzanne, and I enfolded her in my loving arms. Then I gave her a prolonged and passionate kiss on her lips.

“Oh, wow, Frankie!” Suzanne said with obvious delight. “No one has ever kissed me like that before. I like this foreplay stuff. Let’s keep on kissing!”

“Sure,” I agreed. “Hey, the night is young! We’ve got plenty of time to do whatever we want. Isn't that great?” The kissing continued, with me gently pushing her down onto the bed.

I found Suzanne so appealing that my kisses traveled all over her sweet, underwear-clad body. She especially liked it when I began kissing the Minnie Mouse design on her panties. “I think you’re a little bit nutty, Frankie, but I like you...a lot. This is fun!”

I smiled and said, “Suzanne, honey, the time has come for us to do some serious lovemaking.” I slipped out of my briefs to show off my fantastic erection. It was as solid as I could ever recall it being in my limited sexual history.

“That’s the biggest dick I’ve seen so far,” she complimented me as she rose to a sitting position on the bed and gently touched it. “It’s longer than Stewart’s penis and thicker too.” Then she remembered, “Oh, I forgot! You are supposed to be doing everything. Was it okay that I touched your dick, Frankie?” I, of course, let that slight transgression go unpunished. I said nothing but rewarded her with another long kiss on the lips—and another one for Minnie Mouse.

I then put my arms around her and undid her bra. Her exposed tits were quite lovely. They had large areolas and nipples that were poking out. They were just screaming to be fondled. I positioned myself slightly behind Suzanne so I could play with them while I kissed the back of her neck under her brunette tresses. “Ooh, Frankie, I like this, too,” she gushed.

“The pleasure is all mine,” I said without thinking.

“No, it isn’t, Frankie!” she corrected me. I laughed at her cute sense of humor and continued with my sensual manipulation of her terrific titties.

“I just have to fuck these, Suzanne. I can’t control myself,” I told her—which was the honest truth. I moved Suzanne back into a lying position. Straddling her small torso, I placed my hard penis between her breasts and slid it back and forth as I squeezed her tits together. “This is sensational,” I told her. I could only do this for about a minute or else I would come far quicker than I intended. I just laid down beside her and sucked on her nipples for a good five minutes. Somehow, I did not lose my load.

“Suzanne, I think I’ve seen enough of Minnie Mouse for tonight,” I said jokingly. “Let me see the wonderful body part that’s inside your panties.” I slid them off her, kissed the crotch area of them—which Suzanne found very amusing—and tossed them next to my pile of castoff clothing. I then focused my attention on her slightly hairy vagina. It was beautiful to behold! I fingered it only for a few seconds before I positioned myself in the perfect place to lick it. Lick it I did—over and over and over! Suzanne was squirming wildly throughout it. She placed her hands at the back of my head to ensure I would not stop anytime soon. I felt her body spasm and she came to a powerful orgasm. This pleased me because I was genuinely trying to please her—and I had obviously succeeded.

“Holy fuck!” Suzanne said in a loud voice that I’m sure Stewart could hear regardless of where he happened to be in the house. “Can you come her every day and do that to me, Frankie? That would be paradise!”

“We can talk about that later, Suzanne,” I said—and I meant it sincerely. There was no way this was going to be merely a one-night stand. Suzanne was already the best sexual partner I’d ever had in my short life thus far, and we had been at it less than an hour and I hadn’t shot my load yet. That last part was about to change.

“Now it’s time for some serious fucking, Suzanne.” I told her to get on her hands and knees at the end of the bed and prepare for my throbbing dick to enter her from behind.

“I’ve never fucked this way,” she told me. “The boy has always been on top of me, or I’ve been on top of him. This will be a different experience for me. Thank you, Frankie.”

Wow, she was actually thanking me in advance for fucking her in a new way! What a truly amazing girl she was!

Of course, Suzanne’s lovely pussy needed no lubrication at this point. For a second or two, I pondered whether to stop and get a condom, but I dismissed the idea. I was going to do what nature intended: deposit a huge load of cum into this unbelievably sexy teenage girl's cunny.

Accordingly, I got to my feet and moved behind Suzanne’s cute butt. I squeezed her cheeks affectionately and then slid my penis inside her love box. Given Suzanne’s sexual history—which was far more noteworthy than mine—I was surprised that her pussy was still reasonably tight. Still, I easily drilled my dick into her as far as it was physically possible to do. My crotch was slamming into her behind as I thrusted myself forward over and over into my excited little lover. I think I felt Suzanne have another orgasm, but I could not be entirely certain as I was too completely absorbed with my own carnal pleasure at the moment. I uttered a primal groan and fired a supremely large wad of cum into my schoolmate's fabulous pussy. What a great feeling! I didn’t pull out of Suzanne for a while, but when I did, a large amount of my semen dripped out of her. That was a very sexy sight for its former owner.

We were both very sweaty from round number one of what would be a long night of carnal adventures, so I suggested to Suzanne we each take a shower. (Why I didn’t suggest we take one together is beyond me! What an oversight!) Suzanne was first to head to the bathroom to get herself cleaned up. She walked down the hallway, gloriously naked, and encountered Stewart. They briefly conversed.

“Hey, I can see that you two have been having fun, Suzanne! You have Frankie’s cum dripping out of your pussy,” he noted.

“Yes...and we’ve just started, too!” Suzanne giddily informed him. Then she gave him some bad news. “Sorry, Stewart, but Frankie is the best fucker I’ve ever had—by far. He’s also really loving, kind and gentle with everything he does.” Then she added with a grin. “His dick is bigger than yours, too.” As she began to walk away, Stewart slapped her on the bum. Suzanne just laughed at him and continued down the hallway.

For the rest of the night, I continued to be the compassionate lover to Suzanne that I’d promised her I’d be. After we had both showered, we returned to the joys of Suzanne’s relatively small bed—which was great for intimacy. We just cuddled and fondled each other for about an hour. Then it was back to another round of fucking. Suzanne said she desperately wanted to ride me, so being the gentleman that I was, I permitted her to do so. Suzanne amorously bouncing on my dick with her sexy, prominent tits jiggling in front of me resulted in my second cum shot of the night. (I’m not sure what Suzanne’s exact orgasm count was by then. It was at least three.) We alternated back and forth from serious sexual intercourse to loving cuddles well past midnight. Just before I found myself falling asleep with sexy Suzanne comfortably in my arms, I noticed the clock in her room showed 3:20 a.m. I never did put my pajamas on that night.

In the morning, Suzanne and I did plan on having regular sexual trysts whenever we could find a way to make it happen. Once I met her outside the local middle school about 30 minutes after almost all of the students had gone home. (Suzanne informed me she helped with an after-school art program as a volunteer a few times per month.) We went back inside the building. Suzanne guided me to the girls’ changeroom adjacent to the gym. (I had attended this same school for grades six, seven and eight, but I never once set foot in that part of the building!) It was unoccupied, so we fucked passionately in a corner not far from a tampon dispenser. It was weirdly erotic for me, a high school student, to be screwing any girl in a middle school changeroom, even an overage one! Unfortunately, just after we both climaxed, we were literally caught with our pants down by a humorless custodian. He gave us two minutes to get dressed and vacate the building. Thankfully, he wasn't interested in reporting us, so he did not bother to take down our names.

Two Mondays after my thoroughly enjoyable visit to the Ketchum house, I found myself owing Stewart $25 because he had turned the tables on me and recorded a moderately profitable weekend of football wagers. I handed him the proper amount of money when he approached me.

“You’ll note that I’m paying you the full amount in cash, Stewart,” I told him brusquely. “I don’t have a stepsister.”