Roll The Dice One More Time

Chapter 1 -- Carry On Wayward Son

Saint Paul, Minnesota - Saturday Morning, Late Spring, 2054

MacIntosh Brown and his foster mom sit across from each other at the kitchen table. Janice begins, "Mac, you're eighteen today. Legally, you're no longer in the foster care system. So, I'm not your foster mom anymore. We both have to face some harsh realities. You graduate from high school in three weeks. I want you to live here until you finish your senior year. My violent, mentally unstable husband is due back from his out-of-state work assignment in three weeks. You can't be here when he comes back. I don't know what he would do if he saw you were still hanging around, but it wouldn't be pleasant for either of us. So, graduation day will be your first day living on the streets. The homeless shelters in the Twin Cities are full to overflowing; they're not accepting any more occupants. You'll soon be homeless, without a job, money, or a place to sleep. Life on the streets will be difficult for you, MacIntosh. You won't be able to survive unless you find someone to provide you with shelter and food.

"You could always enlist in the military. But as we've discussed before, I think the U.S. Army is a death sentence for you. After basic training, you'll be sent into combat for the remaining years of your enlistment. From what I've read, all three of those senseless wars are brutal and bloody; you'll be lucky to survive six months of combat. So, I think hooking up with a lonely, single woman is your best bet. Because of your age, intelligence, muscular body, and bedroom-blue eyes, you could be an appealing option for a young professional woman. You're certainly handsome enough to attract the attention of most females, but you're going to need something extra to keep a woman interested long-term. Now, I'm going to ask you an important question, MacIntosh. Think very carefully before you answer. Do you want me to instruct you in the critical skills every young man must learn if he's in a serious sexual relationship with an older woman?"

Mac is scared. The prospect of living on the streets is a nightmare that has haunted him for two years. "Yes, ma'am; please teach me what I need to know. I'll do everything you say."

"Okay, MacIntosh. We only have twenty-one days. If we're lucky, we can get in close to ninety hours of training. Let's get started. I need to shower and shave my legs." Janice can't think of a delicate way to ask the next question, so she inquires straight out, "Do you know what cunnilingus is, MacIntosh?"

Yes, ma'am.

"Okay!" Janice thinks, 'Thank goodness!' "MacIntosh, by the time we're through, you'll be a cunnilingus expert. If you can master that one critical skill, most women will keep you around ... permanently! You must be able to consistently give a woman several orgasms using your mouth and tongue. But you have to be mentally prepared for your training, MacIntosh. It's going to be up close and very personal. Please wait for me in your bedroom. You should shower, but don't bother putting on any clothes. I want you nude. Don't look so serious MacIntosh." Janice smiles, "This will be fun for both of us!"

When she's ready, Janice lightly knocks on Mac's bedroom door. Janice wants to give MacIntosh one last chance to back out of his training. She half expects Mac to tell her that he's changed his mind. Instead, MacIntosh instantly opens his door and welcomes her into his bedroom. Janice silently celebrates, 'Hmm, MacIntosh is naked, anxious to begin training, and sporting a beautiful erection.' Janice is wearing an oversized tee shirt. She teasingly slides her panties down her long, bare legs, folds her panties into a mask, and covers Mac's eyes. She secures the makeshift blindfold with two clips. Her panties are damp, and her sexy scent fuels Mac's eagerness.

"All right, MacIntosh, I'll guide you to the bed." Janice reclines on Mac's bed and spreads her legs. "I'm already wet just thinking about what you'll be doing to me. Crawl between my legs and give my vagina a passionate kiss. Remember the basics: kiss, lick, suck, and penetrate. And that's penetration with your tongue, MacIntosh, not your penis. Women are all different. You have to pay attention to how we respond, and if necessary, adjust how you orally service us. I like a man to start by kissing, then licking my pussy. But when I begin moaning, I want you to tongue fuck my soaked pussy ... fast and DEEP. But that's just the first step, MacIntosh. Serious cunnilingus starts when you gently kiss and suck a woman's clitoris. It's a heavenly feeling, MacIntosh. I'm usually able to have three, four, and sometimes five or six orgasms from soft kisses and tender sucking. I've also learned that inserting a small vibrator into my pussy greatly increases the strength and duration of my orgasms. After I come, I've always wanted my lover to gently remove the vibrator and lick it. But I've never been able to convince a man to do that. Since you're now my obedient trainee, MacIntosh, you will suck and lick my dripping vibrator after every one of my orgasms! And when I'm finally satisfied, you will thoroughly lick my anus. I think at least fifteen minutes of enthusiastic ass-licking is appropriate for a young male trainee." Janice pauses. "Have I scared you, MacIntosh? Are you sorry you asked me for instruction?"

"No ma'am; I'm anxious to begin my training ... as you can see from my erection."

"Good. I'll get back to your penis later. By the way, you only have a small chance of experiencing an orgasm over the next three weeks. First, let's measure you. Hmm ... you're almost eight inches. Well above average, MacIntosh. So, your lucky number is eight. At the end of every training session, I'll roll a pair of dice. If the total is eight, I'll give you a mind-blowing, gut-wrenching orgasm. There's one catch, however. A two and a six, or a three and a five won't cut it. To qualify for an orgasm, you'll need double fours! At the craps table, they call that a hard eight, or eight the hard way. So that you know, the chances of rolling a hard eight are one in thirty-six. And you won't be masturbating anytime soon. I bought a new and improved chastity device I'll lock on you after we complete every training session. Well, MacIntosh, let's see what you can do with that tongue of yours. I certainly hope you were paying close attention to my instructions."

Four orgasms and an hour later, a thoroughly satisfied Janice exclaims, "Jesus, MacIntosh, you really were listening to me! I never expected an inexperienced eighteen-year-old boy to perform cunnilingus so skillfully. And you didn't even hesitate when I ordered you to lick my asshole. I eventually had to push you away! Based on your first attempt, I have to admit you're a talented and enthusiastic pussy licker. Don't be embarrassed MacIntosh; that's a compliment! Allow me to catch my breath. You can try some gentle breast kissing while I recover."

"MacIntosh, I'm going to tease you now, using only my hands and fingertips. I'm applying coconut oil as a lubricant." Janice thinks to herself, 'Oh my god, I've never felt a harder cock!' "Apparently, you enjoyed kissing and sucking my clitoris. I think you also loved licking my anus." Janice laughs, "You're a shockingly uninhibited young man, MacIntosh."

"I'm going to bring you right to the edge ... then I'll stop and pinch the tip of your penis. Then I'll do it again, and again, and again until you're begging to come." Janice seems to know the exact moment when Mac is about to ejaculate. She always stops a few seconds before he can reach orgasm ... then expertly teases his cock again, stops as Mac nears the edge ... and continues to stop and start until MacIntosh is pleading for his long overdue orgasm. "NEVER make the mistake of underestimating the skill and ingenuity of an older woman. I'm an expert at denying male orgasms. Now, politely thank me for your intimate massage. I'm waiting, MacIntosh!"

"Thank you, ma'am. I've never felt anything like that before."

"We're not done yet, MacIntosh. One last torment awaits you." Janice crawls on top of MacIntosh and methodically rubs the tip of Mac's cock against her vagina. Then she firmly grasps his shaft and lightly brushes the ultra-sensitive tip against her clitoris. Janice whispers, "Many women like to use this technique to tease their boyfriends and husbands, MacIntosh. I want you to be prepared for this type of sexual torture." Janice giggles when she feels Mac's cock contract and relax every few seconds. MacIntosh is definitely on the edge. Janice relentlessly teases the tip of his rock-hard cock for several more minutes. She suddenly stops, waits several seconds, and without warning, violently impales herself on her young lover's erect cock. Mac feels the liquid heat of Janice's grasping pussy for one fleeting second before she pulls completely off, leaving Mac's rock-hard penis quivering in the cool air. Janice taunts, "I wish I could see the panicked and frustrated look in your eyes right now. Too bad they're covered with my damp panties. Happy eighteenth birthday, MacIntosh. Your orgasm has been denied ... again! Get used to it. Time to lock you up. Now don't move; I need to ice down your cock and secure your new chastity cage."

Janice initiates a second training session in the early evening and a third session after midnight. Both playtimes last about two hours. MacIntosh begins to wonder if he'll be able to survive three full weeks of sex training with his former foster mom. The midnight session is particularly exciting for Janice. Waking an eighteen-year-old boy in the middle of the night, and demanding cunnilingus, makes Janice feel deliciously naughty and cruel. Janice stealthily unlocks Mac's chastity device while he's still asleep. She wakes him by whispering, "MacIntosh, it's time to lick your ex-foster mom's wet pussy and tease her sexy anus with your adventurous tongue. I know you love it, sweet boy." Mac looks half asleep, but his cock is eager and erect.

For MacIntosh, his final twenty-one days and nights with Janice are alternately thrilling and frustrating. Janice never rolls a hard eight, so he's never allowed an orgasm. On the morning of Mac's graduation day, Janice says her final goodbyes. "I wish I could have done more for you, MacIntosh. Don't ever come back here; it's too dangerous for you. I'm afraid my crazy husband will kill you if he finds you here again. Your extra clothes, yard tools, and equipment cart are already in your storage unit. The rental fee is pre-paid for six months. I'm keeping an extra key to the lock on your storage space. From time to time, I might be able to leave a little money, bottled water, or dehydrated food for you. But I've already pawned all of the jewelry I inherited from my mother; money is tight."

MacIntosh, I read once that a fortunate man encounters three women during his life: A woman who saves him; a woman who loves him; and a woman who teaches him all the skills he needs to attract the first two. So, it's one down and two to go for you. MacIntosh, now you must find a woman who will save you ... do it quickly! Stay safe, baby; be strong."

Chapter 2 -- Don't Be Cruel

MacIntosh survives fifteen miserable nights sleeping in public parks and behind vacant buildings. Occasionally, he's forced to scrounge food scraps from restaurant dumpsters. However, a chance encounter with a former classmate provides MacIntosh with an unexpected opportunity. While picking up a few items at a neighborhood supermarket, Mac bumps into a young woman from his high school days.

Evelyn is shocked at Mac's ragged appearance. MacIntosh briefly recounts what happened to him and asks for help. Mac tells Evelyn he desperately needs a few decent meals, a hot shower, and a comfortable bed for a night or two. Evelyn can't understand how an intelligent and handsome boy like MacIntosh could find himself in such a wretched situation. Evelyn's mom is on an extended business trip out of town, so she decides to bring Mac home with her.

"Wait for me outside the store, MacIntosh. I don't want any of my friends or neighbors to see me with a smelly reprobate." Mac has never been called a reprobate before, but he knows Evelyn has an extensive vocabulary and a sharp tongue; he doesn't take her insult personally. When Evelyn exits the store, Mac keeps his distance until she's ready to drive away. "Quickly, MacIntosh, get in the back seat and stay out of sight. I suspect my mom has enlisted several neighbor women to keep an eye on me while she's in Boston. They'll be on the lookout for any boys I might bring home. I'm eighteen and a half, and senior class valedictorian with a perfect grade point average. I'm headed to Stanford on a full academic scholarship ... and my mom is afraid I might do something stupid while she's out of town on business!"

Mac dryly observes, "You mean something stupid like smuggling a smelly reprobate into your home by hiding him in the back seat of your mom's Range Rover?"

Evelyn squeals and her face turns red, "Good point, MacIntosh. Maybe I should drop you off at the car wash. They'd probably need to run you through twice before you came out clean. You'd still be a reprobate, but not a smelly one."

"I'll be quiet now ... and invisible."

"Good idea, MacIntosh. You were always smarter than you looked. Hey, tell me how you went from the second-best student in our senior class ... to a filthy street urchin, in what, half a month? You look like a character out of a Charles Dickens novel. I thought you'd at least get accepted at the University of Minnesota."

"It's a long story, Evelyn. You'll hear my entire, sad tale if you can smuggle me past the neighborhood guardians of female virtue. And to be accurate, I finished fifth, academically, not second."

"MacIntosh, how did that happen? You were a solid second, behind me, with only three weeks of school remaining."

"Yeah, I think it had something to do with a completed term paper I handed over to a beautiful female student."

"Oh, MacIntosh! You said you had another research paper almost ready to go."

"I did. However, Ms. Crawford wasn't impressed with the final product. My class grade dropped from excellent to good. Sometimes that happens. Hey, it wasn't a total loss. In exchange for giving away a term paper I painstakingly researched and wrote, I got a kiss on my cheek from the hottest young woman in school."

"Wait! You think I'm the hottest girl in our high school? There are dozens of young women in our senior class sexier and more beautiful than me. Why would you say that?"

"Evelyn, you feature prominently in the wet dreams of every boy in our school. You need to appreciate that your unique combination of brains, beauty, and sexiness will always outclass the future cocktail waitresses, college cheerleaders, and pole dancers in our school, regardless of how attractive and sexy they might appear at first glance. They're simply not in your league, Evelyn; and they'll never be in your league."

"Why didn't you compliment me like that when we were in high school? And how come you never asked me out, MacIntosh?"

"Because I never had two dimes to rub together. I didn't have access to a car; I didn't even own a bicycle. My clothes were all second-hand. I could only shop in thrift stores. Evelyn, you're going to be rich and successful; heck, I guess you're already rich. I would just be an embarrassment to you. We might as well come from different planets. The best I can hope for is to work as a personal servant for a woman like your mom."

"You ... a servant?"

"Listen, I'm an excellent gardener and an experienced cook and masseur. I'm skilled at all types of home repairs and maintenance, both inside and out. I've cleaned everything from toilets and cat boxes to skylights and ceiling fans. And I'm not bad at doing the laundry, although hand washing women's lingerie is a little unnerving for me."

"Okay, MacIntosh, here's my street. Stay down on the floor and don't make a sound. Hey, I think we got lucky. It appears the nosey, neighborhood women are taking a break. Little do they know what young Evelyn's got stashed in the back seat of her mommy's Range Rover!"

Evelyn maneuvers her vehicle down the driveway and into the triple-wide detached garage. When the door closes, Evelyn says, "You can get out now Mac. Take off all your stinky clothes and dump them in the laundry tub right there. I'd like to burn your clothes, but I'll put them to soak, and later, you can attempt to wash them. Hurry up, MacIntosh; now's not the time for false modesty. Okay, follow me. I need to hose you off like I would a disobedient puppy who's been rolling in manure. This is a good spot. You can't be seen from any of the adjoining properties. I used to sunbathe in the nude here ... until my mom discovered how I got my magnificent, overall tan. She's an attorney; my denials didn't hold up against her withering cross-examination. She told all the women in the neighborhood what I'd been doing. I guess they found it humorous. Some of them still call me Lady Godiva. Here's the garden hose; start washing off the filth. Let's see, I need to grab some liquid soap, baby shampoo, a towel, and Aloe Vera gel. I'll be right back."

[Several minutes later.] "Ahh, you're making progress, MacIntosh. You almost look Caucasian again. How come you're not embarrassed? I'm fully clothed and you're completely naked ... and you've got an erection ... a rather notable erection, as well. Are you into the CFNM scene, MacIntosh?"

"I don't even know what that is."

"Hmm, we'll get back to that subject after I've cleaned you up. Okay, turn around, hands against the wall, feet out, and spread 'em. Wow, you're following my orders. I could get used to this. I feel like a tough policewoman. You're suspiciously obedient, MacIntosh. Before we do anything else, I'm going to thoroughly soap every inch of your muscled body. And I'm starting with your nasty ass crack."

[Ten minutes later.] "You know, I kind of enjoy soaping the body of a handsome young man. It's quite exhilarating ... and educational. You're a new man now. Your hair is squeaky clean; you even smell good. But you've still got a hard-on, MacIntosh. How long has it been, Mac, since your last orgasm? Hmm? Tell me, Mac! I think I'll apply some lubricating gel to that persistent erection of yours. Let's see if you can be more forthcoming when you're on the razor's edge of an orgasm for several hours."

"Evelyn, I haven't had an orgasm in so long, I don't remember what one feels like."

"That's not a satisfactory answer. How long has it been, Mac? And why has it been so long? Answer me!"

"At least two months. For a long time, I was worried about what would happen to me after my eighteenth birthday. It's all I could think about. For the last fifteen days, I've been living like an animal, just trying to survive on the streets. And during the three weeks right before we graduated, I was ..."

"MacIntosh, what happened to you during those three weeks? Tell me!

MacIntosh hesitates before answering. The tone and cadence of Mac's explanation sound like a criminal confession. "A mature woman taught me to sexually satisfy her in every way you could possibly imagine. She proved to be a talented cock teaser, and incredibly skilled at denying my orgasms. I begged her to teach me everything I needed to know to keep a woman happy and satisfied. Sometimes my training was exciting, and at other times, it was humiliating and embarrassing. I'm ashamed to admit, I was nothing more than her obedient sex toy for three long weeks. But I always thanked her for teaching me those survival skills. Evelyn, I'm ... I'm not proud of what I've become, but circumstances have forced me into that role. It's not the career path I expected or wanted; however, it's where I ended up. For now, I believe it's my only option if I want to stay off the streets."