Date: Fri, 20 Jun 2008 09:38:17 -0700 (PDT) From: Beautiful Creamer Subject: Dating Pretty Boys -- Part Five Dating Pretty Boys -- Part Five By Beautiful Creamer One -- An Educational Date The pretty boys' date with their two teachers, Mr. Stiffman and Mr. Spunkmore, proved to be every bit as frightening and ball-draining as the boys had imagined. Since the boys had gone way out of their way to humiliate the men on the earlier date, when the boys could do anything they wanted, the boys expected payback on the "men rule" date. As agreed, the handsome young teachers picked the boys up at six at Rickey's house. As instructed, the boys ate supper before their date; there would be no ritzy, humiliating, public meal that night. Also as instructed, the boys were standing on the Fellatos porch, awaiting the toot of a horn from the men's car. There would be no humiliating, parental interrogations that evening either. Bobby slid into the seat next to Mr. Stiffman, the driver, and Rickey got into the backseat with Mr. Spunkmore. Both boys took it as a good sign that the teachers greeted them with hot, tonguey kisses. Maybe all was forgiven. Maybe. The men took the boys to a nice hotel, where they had taken the precaution of registering earlier in the day. Then they sent the boys through the backstairs to room 236, where the men joined them and everyone tumbled into the room. After triple-locking the door, the men ordered the boys to strip naked. So far so good, Rickey and Bobby thought. They're going to fuck us as often as their advanced years (31 and 32) permit and that will be that, he imagined. Not exactly. The men got naked too -- another good sign. But then things turned. In a voice that the pretty boys had only heard from Mr. Stiffman when he was enforcing discipline on the playground, the man said, "You little brats are going to pay for what you did to us last time and you're going to pay now!" With that, Mr. Stiffman grabbed Bobby by the wrist and somewhat harshly flung him face down across his naked lap. Mr. Spunkmore did the same with Rickey. Before the frightened boys could react, each felt a firm hand flashing down on the bottoms that they thought were just for teasing, sitting, pooping and fucking. Bobby saw a galaxy of painful stars as Mr. Stiffman administered a hard and quite thorough spanking. Bobby screamed in pain, which only served to stiffen the man's already enflamed cock. No one had spanked Bobby since he was about eight. His Daddy wanted to fuck him, not spank him (Duh!) and his Mom was never a spanker. He was in what he considered to be agonizing pain. Mr. Stiffman was really enjoying spanking the naughty boy! And so was Mr. Spunkmore! Worse, the men were clearly and visibly aroused by the act of well-deserved punishment! Was this to be the boys' date and fate for the next 12 hours and 15 minutes? Bobby couldn't endure that. No matter what deal they made. He would call 911 if he had too. Scream his guts out until someone investigated. The pain was intense... And yet. The man slowed a bit in his spanking. Repositioned Bobby so that the boy's inexplicably stiff cock was nestled between Mr. Stiffman's warm, hairy thighs. The man was dominating Bobby. And Bobby loved being dominated by a strong, handsome man. Then the pain wasn't as bad. Softer swats or something. He looked over at Rickey, who had stopped crying and seemed to be concentrating on an impending orgasm. Bobby knew that look well. Bobby was probably showing Rickey a similar look, since his painful experience was morphing into something painfully erotic. A cum was on its way, but it wasn't like a normal cum. It seemed to be building differently -- the way he had felt the first time he orgasmed with a man's cock stuffing his bottom. Slow buildup usually meant...oh! He was about to be slammed by an 18-wheeler. And he couldn't get out of the road. Wham!!! What a cum! Blast after blast all over Mr. Stiffman's inner thighs and the hotel carpet. In the throes of orgasm, he caught Rickey's eye. Rickey was experiencing the same gut-clenching joy. Well, well. The evening already introduced the boys to something new. More was imminent. When the boys had finished their excursions to paradise, the men ordered the boys to get on their knees and suck the men's cocks. A welcome order indeed. Except that the boys couldn't sit on their painful haunches. Fortunately, the men were so aroused by spanking the little miscreants, that they filled the boys' mouths with hot cream within minutes. Since everyone was obviously having quite a good time, the boys were hopeful that the agenda would move to a more standard program of ball-draining, man-boy sex. Not yet. The pressure on their balls having been relaxed for the moment, an uncharacteristically rough duo of teachers marched the boys to an open corner of the room, then had them put their hands on their heads and face the wall. Then they ordered the boys not to look around or at each other. There was to be no talking and no touching of themselves or each other. Fearing (yet considering the pleasures of) more spanking, the boys obeyed. They stood there for a good 15 minutes, during which they heard quite a bit of drawer-opening and closing and soft rustles. What was happening? And more importantly, what would happen next? Mr. Spunkmore broke the suspense by saying, "All right boys, you can turn around now. Let's get some soothing cream on those red bottoms of yours, you poor kids." Poor kids? Weren't those thuggish teachers the perpetrators of that redness? Still the boys were quite willing to forget and fuck. Curiously, they noted that a sheet was covering some flat objects on the room's lone, king-sized bed. Hmmmm. Mr. Spunkmore took Bobby to his manly bosom that time, tsk-tsking the damage his fellow teacher had done to the world-class treasure that was Bobby's ass. Bobby played it well, whimpering and teasing as the man kissed his lips to "make it all better." Mr. Stiffman was kissing Rickey and began rubbing soothing cream all over the area his fellow teacher had ravaged. The boys cooed in delight as the men attended to them. When the flames in their bottoms had died down sufficiently, they sat on their men's laps and submitted sweetly to kisses and prick-tickles. But that was just a warm-up. "Now that we've settled that score," Mr. Stiffman said, "we're going to introduce you to something new and exciting." Oooooh. The pretty boys liked new and exciting. Their pricks jumped in their lovers' hands at the thought. Without further pause, the men led the boys into the bathroom. Mr. Stiffman sat on the edge of the tub. Mr. Spunkmore sat on the toilet. Each had a razor and shaving cream in his right hand and a wet washcloth in his left hand. Mr. Stiffman began to wet Rickey's left leg, then lather its entire length. Mr. Spunkmore did the same for Bobby. They were shaving the boys' legs! The boys had only a suggestion of hair there, but the men gently scraped it off. Then they went to work on each boy's armpits. That tickled! And the suspense grew. What was happening? The boys were a bit worried that the men might relieve them of their soft, sexy little tufts of pubic hair, but that was allowed to remain. Satisfied with their work this far, the men gave each boy a loving, careful sponge bath with a soapy washcloth, stopping frequently for breathy kisses. When the cleaning was done, Mr. Stiffman produced two containers of scented talcum powder, which the men applied liberally and lovingly to the boys' midsections and legs. Something big was happening and the boys had no clue. Finally, the four lovers left the bathroom and returned to the bedroom, where Mr. Spunkmore removed the sheet and revealed... Yes, revealed... Something the boys wouldn't have guessed in a million years. It was girls' lingerie. Lots of it. And really girlie stuff too. Stockings - the fully-fashioned, reinforced-heel-and-toe kind like they wore in the 1950s. Garter belts -- the ruffled ones. Baby-doll nighties so sheer you could read 6-point type through them and so short the entire pubic area was brazenly exposed. In two colors -- black and pink. Huh? Rickey actually asked, "Who's that stuff for?" Then he realized. Oh my. Rickey and Bobby were taken back a peg with what they saw. Did these, these men expect them to dress like girls and pretend to be girls? Wearing all those pretty, sexy things that caressed the body and excited the senses? Taking the men's cocks up their bottoms with the men pretending Bobby and Rickey were girls. As if the real Rickey and Bobby weren't boys. Hmmmph! The pretty boys weren't girls, they were boys. It was wrong. Which is what made it very exciting. Mr. Spunkmore said to Mr. Stiffman, "I think the blond would look better in black, don't you?" "I agree. Do you want to dress her?" "Gladly" Her? Her? Bobby was ending this right here. He was no "her." But then. Mr. Spunkmore held a black, seamed, fully-fashioned, reinforced-heel-and-toe stocking next to Bobby and brushed it across the sissyboy's freshly shaved leg. Bobby shuddered. He watched in fascination as Mr. Spunkmore rolled the stocking into a doughnut and placed the boy's pretty, pointed toe within the stocking's silken walls. Slowly, sensuously, Mr. Spunkmore rolled the stocking up Bobby's leg. Bobby gasped in surrender to the fulfillment of an apparently undiscovered desire. Rickey watched in fascinated horror as his friend succumbed to his alleged feminine side. No way Rickey would allow that. No way. Until Mr. Stiffman rolled a tan, seamed, fully-fashioned, reinforced-heel-and-toe stockings along the brown-haired boy's lovely leg -- all the way up. Then matched it on his other leg. Both boys looked at each other sheepishly, ashamed to be enjoying something so wrong, so much, in full view of the love of his life. The men carefully hooked garter belts to the boys' slim hips -- black for Bobby, pink for Rickey. Then they slid a black babydoll nightie over Bobby's head and a pink one over Rickey. Girls didn't hold much sexual attraction for Bobby nor Rickey. But their little peters were stiff as nails looking at each other that summer evening. They kept sneaking peeks at each other as the men inexpertly but determinedly applied lipstick to the boys' kissable lips. Finished with their temporary and certainly unnatural transformations, the men stepped back to admire the "girls." Bobby and Rickey were embarrassed but kind of proud that they were giving Mr. Stiffman and Mr. Spunkmore the biggest, drippiest stiffies the men had ever had. Then Mr. Spunkmore said, "Why don't you go look at yourselves in the mirror?" Semi-reluctantly, they did. Now dressing up like girls was not something Bobby and Rickey ever considered doing, would do on their own, or planned to do again. But that night, in that hotel room, with those men, they had to admit, they looked smokin' hot. So hot that they knew, with a little effort, they could pass for girls and steal the men and boys from every girl in their school. Or any school. If they wanted to. Dressed as girls or dressed (or undressed) as boys. Looking in the mirror, they admired each other and themselves for a good, long time until Rickey broke the spell by kissing Bobby, lipstick to lipstick. That was strange. But very sexy. The pretty boys got into a hot clinch, which the men had to break up, since they wanted all that "girlie" spunk for themselves that evening. And night. And next morning. And they got it. The men quickly had the boys side-by-side, on the bed, on their tummies. The men lifted the nighties, exposing the pretty boys' perfect bottoms. The perfect pink globes were deliciously framed by the filmy skirts of the babydolls, two thin garter straps and the dark, multi-shaded tops of the boys' stockings. The men savored the sight for a moment, then they got onto the bed and dug between the boys' bottom cheeks with their hungry tongues. Spurred on by the realization of a long-suppressed fantasy, the men had the boy's "pussies" sopping, then full of hot, hard cock, then full of sperm. The boys and their girlie lingerie were drenched in sperm before the overnight date was over. And the pretty boys' asses and mouths got an excellent workout. The teachers were enflamed all night, overcoming their "age disability" and fucking the pretty boys in a manner and frequency equal to teenagers Matt and Derek. Amazing how excited you can make a man if you just play along a bit with what he wants. Yes, that night the teachers taught their students two new lessons -- "S&M Lite" and "Beginner Crossdressing." Which added the great prize of variety to the boys' sex lives. Do you see now why we tell kids to stay in school? Two -- Tuesday evening elsewhere Mark and Derek did not have a great Tuesday evening. After four consecutive, delicious nights of sex with pretty boy Bobby, Mark missed his lover tremendously. After the night of his life with Rickey, Derek was a bit edgy himself. As he tossed himself off in his lonely bed, he dreamed of the delights he and Rickey would enjoy the next night. Randy was doing somewhat better, having just had his young testicles emptied several times during the afternoon of his life. But if Mark and/or Derek had called to suggest a quick, dirty liaison with Randy, he would have surely said yes. And found a way to meet them. See why there should be a prettyboyhookup.com? Anyway, while Rickey and Bobby were entertaining big cocks in their pretty bottoms, Randy was playing Parcheesi with his Mom, Dad and sister. And losing. He couldn't concentrate because Daddy was there. And Randy kept wondering what was going to happen when Daddy tucked him in later. He wondered if he should tell Daddy about his new friends. And how they "helped each other out" all afternoon. Randy decided compromise was best. At supper he told Mom and Daddy all about the nice boys he met at the pool and how he, Rickey and Bobby had a good afternoon at Bobby's house. Mom told Daddy how happy she was that Randy had new friends. Daddy was a bit uncomfortable with the notion that he had fucked one of Randy's new friends four days earlier. Fonda complained that they were having meat loaf again. At bedtime, Randy spent more time than usual checking himself out in the mirror. His shorty, summer pajamas made him look very young, his face was very pretty and his body was exquisite. In short, he was totally fuckable. Though, at that point, he didn't even know that boys were fucked. Randy got into bed and lay there waiting for Daddy. It had been more than five hours since his "little bag" had been emptied. He hoped Daddy would "help him out." Randy knew that he could "help himself out" if worst came to worst. But that seemed like a last resort thing to Randy. Daddy appeared, smiling sweetly at Randy. Daddy had always been a good father. Long before the "helping out" began. Randy loved Daddy and likewise. Daddy sat on the bed to Randy's right. As he pulled the sheet off Randy, he said, "I'm glad you have new friends, Randy. Do you like them?" Randy squirmed a little as Daddy unbuttoned his pajama top and unsnapped his pajama bottom, exposing his bare chest, puffy nipples and stiff willie. "Oh yes, Daddy," he said. "Bobby and Rickey are nice boys." "It's so stiff," Daddy said as he ran his hand along Randy's penis. "Are you excited?" Randy blushed, looked down shyly and said, "Oh yes, Daddy." Daddy smiled and kept stroking. "Good. A young boy needs excitement in his life. Did you and your new friends touch each other's penises today?" Randy blushed harder and told the truth. "Yes, Daddy. We kissed too and made each other spurt." Delighted at Randy's honesty, Daddy stroked on and said, "You're a very pretty boy. It's no wonder they wanted to share that fun with you." Randy blushed again as he gasped and panted from Daddy's manual attentions. Daddy got Randy pretty "close" and then he stopped. And asked a big question. "Was that all you and your pretty new friends did today?" "Oh, yes, Daddy. We kissed and hugged and tickled each other's penises until we spurted all over each other. Please don't stop, Daddy. It felt so good." Daddy smiled and reached for a jar of lube. Randy had wondered why Daddy was "tickling him dry." It was so much nicer when he used slick stuff. He wriggled invitingly to Daddy as the man got three fingers nice and slick. But Daddy didn't reach for Randy's aching penis! Instead, he lifted the boy's ball sack and reached under and ... Aahhhhh! What was Daddy doing? He was sticking his middle finger into Randy's bottomhole!!!!!!!!!! Randy didn't know that was even possible. It felt...nice. Really nice. Then Daddy added a second finger. Oh. That was even better. The third was beautiful and he thought he heard Daddy say, "Did they do that for you, Baby?" Randy thought he answered Daddy but he wasn't sure because Daddy's fingers found something inside him -- something that made him squeal (softly, thank goodness, so Mommy didn't come running). Something that made him very excited, even though Daddy wasn't even touching his willie. Then Daddy said something that sounded like, "And did those pretty boys show you this?" Randy wasn't sure that Daddy said that, because he was biting his lip trying not to scream or grunt because of the most incredible feelings he had ever had. And then they got more incredible. After Daddy's alleged second question, he took Randy's stiff little cock fully into his mouth and lovingly licked the head. As he massaged the boy's virginal, ultra-sensitive prostate. Randy sat up straight and, with amazing presence of mind, threw both hands over his mouth to muffle his scream of surprise and lust as he emptied his testicles in one wrenching heave into his father's mouth. Daddy continued sucking Randy's dribbling cock and fingering his boyish pussy until the spent boy lay back. Then Daddy gave the boy's cockhead a sweet kiss, stood up, bent over to give the boy's mouth a tonguey smooch, and pulled the sheet over his loving son. Then he said, "Good night" and left the room to rejoin his wife. Randy could barely focus his eyes, as he sought the license number of the truck that just hit him. Then a very naughty notion formed in his head. Mom and Fonda were going to early-morning skating again the next day. He would be alone with Daddy! Yummmmmm. Three -- Randy discovers a new food group Unlike the previous night, Randy slept very well. An empty ball bag is the best cure for insomnia. When he awoke on Wednesday morning, he awoke very nicely. Randy was on his back, chest and pubic area still exposed from Daddy's naughtiness of the previous evening. Daddy was completely exposed -- bare ass naked. And he was lying on Randy's right. Sucking Randy's cock. Pausing now and then to give the boy's balls a nice tongue bath. When Daddy saw that Randy was awake, the man did that naughty thing again with his big, rough, lubed fingers in the boy's tight pootie. That naughty, intense, magnificent thing. The thing that made Randy want to scream. Daddy stopped sucking and fingering for a moment and said, "Good Morning, Sweetheart. I'm going to show you a little more of last night's lesson. This morning you can make all the noises you want. Mom and Fonda are gone. Noises make it good for you and the other person who's helping you out." Then Daddy resumed his welcome attack on Randy's erotic senses. The boy was in the high-rent district of heaven. Grunting. Arching his back. Squealing sissily. Then screaming as Daddy pushed him off Cum Cliff. Daddy kept sucking and fingering. Licking and swallowing. Making it last as long as it lasted. Then Daddy moved up to engage Randy in deep kissing. Feeding Randy a taste of his own cream. They kissed hotly for a long time, stroking each other's cocks until Randy broke the kiss and said, "Oh, Daddy. I had no idea that anything in the world could be that good." Daddy beamed. "There's lots more to show you, Honey. I'll show you everything men and boys do for each other. But slowly. Maybe you could do something for me. Now." Oh. Did Daddy want Randy to suck his cock? The way Daddy had just sucked Randy's? Could Randy do that? Wasn't that gay? Randy knew he wasn't gay. Daddy wasn't either. He would just be relieving Daddy. Doing something Daddy did for him. Something fantastic. He could do it! "OK, Daddy," he said meekly. "But I don't know if I'll do it right. And it's too big to fit in my mouth. I think." Daddy smiled. "You'll do fine. Just keep your teeth out of the way. And it's really about licking, not sucking. I really appreciate it. It hurts me right now I need relief really badly. Oh, that's very nice." Randy held Daddy's cock in his boyish hand and looked at it closely for the first time. Tentatively, at first, he kissed the head. The drooly part, by the peelips. He tasted the little pearl that had formed at the crest of Mount Peeny. A bit sweet -- not salty. Not bad. Daddy liked that. Then Randy proceeded to a bit more active measures, licking around the perimeter of his Daddy's cockhead. Giggling a little at Daddy's soft moans. He must have been doing it right. Randy wasn't sure if he would be able to cap the head with his little mouth, but he wanted to try. He stretched his mouth the way he did when bobbing for apples at Halloween. Then he breathed deeply and dove into Daddy's stiff cock. Daddy groaned very loudly, which Randy liked a lot. He was proud that he had gotten the head and about two inches of Daddy's cock into his mouth. Remembering what Daddy said about no teeth, Randy sucked and sucked, using his tongue very nicely. Daddy couldn't believe his good luck. His son was already a better cocksucker than his wife. And she was good. Daddy couldn't endure much more of that love assault on his manhood and, after five minutes of sweet torment, he cried out and began to pump a quart of sperm into his cutie-boy son's stretched mouth. Randy wasn't expecting that and he gagged a bit at first. Much of the "boy's big reward" dribbled out of his mouth and onto Daddy's pubes and balls. Randy managed to swallow the rest, then lovingly lick the cum he missed from its resting place on Daddy. Where did he learn that? Nobody taught Mozart to compose. Some people are just naturals. Randy slid up to kiss Daddy, snuggling and rubbing nicely. Until Daddy couldn't help but notice that Randy's "pencil" had refilled with lead. The boy's stiff peeny was rubbing nicely against Daddy's hairy tummy as they kissed. Which gave Daddy the idea that the boy's testicles were once again in dire need. And a good Daddy doesn't let his boy suffer. So Daddy kissed his way from Randy's mouth to the boy's penis. Licking his alabaster neck. Butterfly-kissing his bosom. Licking and sucking each puffy nipple until the boy begged his Daddy for relief. Softly, teasingly licking out Randy's "innie." Lightly kissing each of the boy's pubic hairs. Then, when the boy was frantic with lust, engulfing Randy's cock and balls inside Daddy's hot, wet mouth. Randy squeaked with joy as Daddy expertly and passionately licked and sucked the boy's tender center of erotic pleasure. Randy saw new constellations when Daddy's attentions made him expel his hot juices into Daddy's loving mouth. Daddy sucked, licked and swallowed, remembering the joys of sex with Andy and Sandy, the young neighbor boys he had loved as a teenager. And his recent encounter with that little piece Rickey. This was better. He already loved his son. Their actions deepened their love. And he was teaching Randy valuable life lessons. Which the boy was apparently learning well, since he was moving south to take Daddy's rapidly recovering cock into his sweet, young mouth once again. Randy was upset when Daddy said, "No, Randy!" Was Daddy going to deny himself the pleasure of a second cock-sucking? And deny Randy the pleasure of the act? Not bloody likely. "Let me stand up, Baby," Daddy said. "And you get on your knees. That's what a boy does for a man." Mmmmm. On his knees! Randy was already enjoying the power of submission. Moving quickly, Randy slid to his knees and buried his face in Daddy's crotch. Smelling his manly musk. Then licking his hairy balls. Yum. That took Daddy from semi-hard to really hard. And made Randy abandon Daddy's balls and set him onto licking, kissing, sucking and generally adoring the paternal pole. Keeping eye contact with Daddy as he grunted and licked happily. Soon, Daddy was making those twitches again. Those, pre-blast twitches. The same kind Randy got. Nice twitches. Then Daddy cried out something that sounded like, "Oh, shit!" but Randy wasn't listening. He was trying to swallow the six thick globs of cum that Daddy was shooting into Randy's mouth. By his count, he gagged down about 3.5 globs. The rest went onto his face, chin, and chest, with some drops even dribbling onto his penis. A job well done by any standard! And that was all father and son would do that lovely morning, as each sorted out his feelings on the matter. Daddy worried he had gone too far too soon. But did he want those little tarts Randy was hanging out with to be the ones to teach Randy about sex? Or some teacher or neighbor who hired Randy to mow his lawn? No. It was his Daddy's responsibility. Randy's feelings were much less conflicted. He loved sucking his Daddy's cock. And having his own sucked as well. All he wanted to know was, when could he and Daddy do it again and who else's cock could he suck? He was pretty sure that, later that day, he would be sucking and being sucked by Rickey and Bobby. He and Daddy kissed for a while, then they got up, had breakfast, got dressed and went to the pool. More about the pretty boys soon. I welcome your comments at beautifulcreamer@yahoo.com. Other stories on nifty: "The Little Prickpleaser" (gay incest) August 22, 2007 "Sweetyboys" (gay young friends) August 31, 2007 "Boarding-School Bedmates" (bisexual adult-youth, though it's quite gay) May 5, 2008 "After-School Stroke Club" (gay high school) May 28, 2008 "Pretty" (gay adult-youth) May 21, 2008 "Hotel Management" (gay adult-youth) June 2, 2008