Jesse heard the doorbell ring and knew that is was Rob, come to pick her up for their date. She was still in the shower, one towel wrapped around her hair, another around her otherwise naked body.
“Want me to get that for you?” her sister Jill asked, poking her head in as the bell chimed again. Jill was 17, two years younger than her only sister. They both lived with their mother, who had been widowed fifteen years before. “It’s probably Rob, picking you up for your night out with him.”
“Just tell him I’ll only be a minute more.” Jesse agreed. “Thanks, sis.”
Jill didn’t say anything; she went downstairs to let Rob in. He had a bouquet of flowers in his hands.
“Are those for me?” she asked, batting her eyes at him.
“This one is.” he replied with a smile. He pulled one of the roses out of the bouquet gracefully, not disturbing the rest of the bunch. “It’s not as pretty as you are, though.”
“A flower AND a compliment.” she sighed. “One more nice thing like that, and you get a kiss, even if it is Jesse’s night.”
“Where is Jesse?” he asked, looking around the living room.
“She’s upstairs, doing her hair.” Jill replied. “Mom’s at work, so you’re stuck with me until she comes down.”
“Oh, I wouldn’t call it stuck, Jill.” he said. “I really enjoy your company. Shall we play a game while we wait?” he asked. “If I know your sister, doing her hair means that she’s not dressed yet, and that means at least half an hour.”
“All we have for games is cards, I’m afraid.” she told him. “What do you want to play?”
“What games do you know?” he asked.
“Well, the only one I’m really good at is Twenty-One.” she said.
“Okay, let’s play that.” he agreed, and she went to get the cards as he set the flowers on the dining room table.
He watched her butt sway from side to side in her mini as she walked across the kitchen to get them from the junk drawer. She sat down at the glass topped table in there and called him over.
“Let’s play in here.” she said. He came over and sat across from her. “You deal.” she said, handing him the cards. He took them out of the box, pulled the jokers out, and shuffled them quickly.
“This is a betting game, you know.” he told her. “What are we going to gamble for?”
“Deal the first hand and the winner can decide.” she said, smiling. “Anything goes, okay?”
“Are you sure about that?” he asked her, eyebrows raised. “Anything can mean… well, ANYthing!!”
“Just deal them.” she said. “Unless… are you afraid you’re going to lose?” she grinned.
“Yeah, right. You’re too young and innocent to ask anything that might embarrass me.” He dealt the first hand, giving her a three and himself a ten.”
His words stung her a little, and she resolved herself to change his opinion of her, no matter what it took to do it. “Young and innocent! How dare he!” she fumed silently, but no a trace of her thoughts showed on her face. She looked at her hole card, her face inscrutable.
“Um, hit me?” she said, hesitantly. She was familiar with the basics of the game, but not the finer points of it. She got the Queen of Clubs. “Stay.” she told him.
He flipped over his hole card. It was an ace. “Twenty one!” he said jubilantly.
She looked steadily at him. “What did you win?”
“I don’t know… something shocking. Something you’ve never done before. How about… a kiss?”
“Oh, please!” she said, her bitterness showing a little as her voice cracked. “My Mom has kissed me plenty of times.” “He only thinks of me as a little kid!” she thought.
“I’m not going to kiss you like your Mom does, Jill.” he said.
“Oh.” she said softly. “Maybe he doesn’t think of me that way.” she thought.
Out loud she told him, “Deal the next hand. You have to give me the chance to get it back. You’re right; I’ve never kissed a boy before.”
“Fair enough.” he said, sweeping the cards aside and dealing out the next hand. This time, they both got kings showing.
“Umm… hit me?” she said uncertainly. He flipped her a nine.
“Busted.” she said, showing him a four in the hole. “Two kisses.”
“Nope.” he grinned at her. “First base!”
“Deal them again.” she deadpanned. “I know you’re gonna lose this time.”
She got a nine showing, and he got a six. “Stand.” she said, grinning. He took one card, a five, then showed her twenty one again, a jack in the hole. She had twenty, as her hole card.
“Oh, no.” she moaned. “One last time, double or nothing!”
“Double third base is a home run.” he said quietly. “That’s all the way, you know. Right now all you have to do is make out with me while I get to feel you up.”
She blanched. “I think you know I’m a virgin.” she said. “I don’t wanna go all the way yet.”
“I know.” he said. So, if you lose this hand, I’ll only make you have to do a blowjob, instead.”
“Will I have to?” she whispered.
“Not if I lose this hand.” he said.
“Okay, deal.” she said nervously. “Oh, please let me win?” she muttered under her breath. She was a lot braver in thought than deed.
He flipped the cards out quickly. She got a two. “Hit me.” A five. “Stand?” she said, hesitantly.
He had an eight showing, and flipped over a queen. “Eighteen.” he said. She showed her hand, another queen, for seventeen.
“Time to pay up, I suppose.” she said resignedly. “Nobody can call me a welsher.”
“You don’t have to if you don’t want to.” he told her. “I’ll let you out of all of it, and I won’t ever call you a welsher for it, either.”
“Can I try one more hand?” she asked. “If you win, you can have me, all the way. “If I win, you still get the kiss, with first base, but I don’t have to do anything else.”
Just then, they saw Jesse enter the room, looking delicious in her white silk peasant blouse and hip hugger jeans.
“Oh, playing cards!” she said. “What’s the game?”
“Twenty One.” Rob answered.
“WHo’s winning?” Jesse asked.
“Rob is. “ Jill answered. “So far, I owe him a blowjob, but he has another offer on the table he hasn’t decided on yet.”
“What’s the offer?” Jesse asked.
“My virginity if I lose. First base if I win.” she replied.
“Deal three hands.” Jesse offered. “If I win, you get nothing, Rob. If Jill wins, you still get the blowjob, but from me, instead. And if you win, we’ll both give you the blowjob at the same tome.
“One more thing.” he said. “The big loser has to go all the way if I win.”
The sisters looked at each other and nodded. Rob gathered up the whole deck, shuffled them all together briefly, then dealt out three hands. He gave Jill a seven, Jesse a four, and himself an ace.
“Stand.” said Jill. “No, hit me.” She got a King. “Damn! You better win, Jesse.”
“Hit me.” Jesse said. A three. “Again.” Another three. “Stand.” she said, looking at Rob smugly.
Rob turned over the Jack of Spades. “Blackjack.” he said quietly. “I win.”
“No, wait, I have twenty one, too!” Jesse objected, showing her ace in the hole.
“Jesse, Blackjack is the highest hand in the game.” Rob told her. “See? I needed fewer cards than you, so it’s the better hand.”
“We lost, Jesse, fair and square.” Jill said.
“One more hand!” Jesse cried out, desperately.
“Okay.” said Rob. “I still get the double blowjob, no matter what. However, you both have your virginity on the line. If either of you win, you don‘t have to do it. If I win, I get to have both of you. At a time and place of my choosing.”
“No.” said Jill. “We haven’t won a hand yet. We’ll just do the blowjob together and that’ll be the end of it.”
“Jill, please!” Jesse begged. “There’s only a one in three chance you’ll have to spread your legs for him! If you say no, I WILL have to! I already lost my cherry to him.”
“Well, technically, so did I.” Jill said, ruefully. “Okay, Rob, one last hand.”
“Okay, ladies, one last hand.” Rob said, dealing them out again. “But no matter what happens this round, I still get head from both of you right after this.”
Jill got a ten, Jesse got a two, and he took an eight.
“Hit.” Jill said. She got a four. “Stand.”
“Hit me.” Jesse said. She got a ten and grimaced. “Busted. Hope you got good, Jill.” she said.
“Stand.” Rob said, showing eighteen. “Whatcha got, Jill?”
Jill smiled wickedly at her sister and showed a face card. “Twenty four.” she said. “We lose.”
“You bitch! You hit on twenty? You just lost on PURPOSE!!!” Jesse screeched.
“Yeah, I did.” Jill said, calmly. “Are you going to welsh?” She looked over at Rob. “Come on, let’s go into the living room.”
Rob got up and walked around the table, taking Jill’s arm along the way. He slid his other arm around Jesse’s waist and helped her to her feet.
“Come, my dear, you can’t say that didn’t win that last hand fair and square. Besides, it’s not time for the last step yet. I want my double blowjob right now.”
“I’ll do the blowjob with her. I already promised you that.” Jesse
said, letting him lead her reluctantly into the next room. “But that’s all you get from me, because she cheated!”
“Fine.” he agreed. “But if you’re going to welsh on the second half of the bet, you’re going to suck me off naked!”
“Wh-what?” she gasped, shocked. “No!! That wasn’t part of the deal!”
“You heard me.” he said, pulling her buttons free of the loops, moving from the bottom of her blouse to the top after tugging it out of her jeans.
“Rob, wait, please!” she begged, trying to push his hands away. He had let go of Jill altogether, needing both hands to get Jesse’s shirt open. He was halfway done when she seized his wrists and made him stop. “That wasn’t part of the deal!” she said. “You’re just making stuff up! I never agreed to suck it naked!”
“Rob? Forget about her. I’ll do it naked for you. I’ll let you go all the way with me, too, as long as you promise to be gentle.” She looked at him steadily. “I’ll do anything you want to do. Anything.”
Rob looked at the younger girl and smiled, turning to her. “Thanks, Jill. I’m glad one of you is no welsher.” he said. “I believe the first bet was for a kiss?”
He put his hand to her chin and lifted it slightly, allowing his lips to ever so gently meet hers for a long moment.
“And now, first base.” she whispered. His hand trailed down her neck to the swelling mound of her breast, caressing it through her thin cotton T-Shirt. They kissed again as his other hand went to her hip and pulled her a little closer, rising up under the hem of her shirt.
She moaned into his mouth as his thumb found her nipple and rubbed it erect.
“Jill, what are you DOING!!” Jesse exclaimed, as Rob lifted the shirt off her sister, with little help.
Her sister looked at her with steel in her eyes. “I’m doing exactly what you SHOULD be doing. Living up to the bet we lost.”
“A bet we should never have made.” Jesse said, bitterly. “A bet you lost on PURPOSE!!”
Jill started to reply, but Rob took that moment to caress one of Jill’s nipples with his mouth, laving it with his tongue. Jill let out a moan of pleasure instead of the retort she had planned.
“I guess I’ll leave you two alone, then.” Jesse said, the bitterness evident in her voice.
“I guess you won’t.” Rob said. “It’s time for you to suck my cock.” He raised his hands to Jill’s shoulders, gently pushing her down to her knees. “Now, get over here and help your sister.”
When Jesse was in reach, he reached out and cupped her chin, drawing her near for a kiss. His other hand unerringly unbuttoned the last three clasps of her silk blouse, then pushed it back off her shoulders. His right hand slid slowly down her bare back and deftly unfastened the clasp of her bra one handed.
He could feel Jill unbuckling his belt. He began stroking her hair after sliding Jesse’s bra straps off her shoulders. He paused a moment and stripped his T-shirt off over his head.
He looked at Jesse standing topless before him for a long moment, relishing the sight of her bared breasts before him. They were on the smallish side, but quite firm, and were capped by quarter sized pink areolae, surrounding surprisingly well defined nipples.
Jill’s hands had been busy, and she pushed his opened pants down over his ass, down his legs, and then she helped him step out of them. He put both hands on Jesse’s shoulders to steady himself as he stepped out of his jeans, and she took it as a sign to go to her knees beside her sister. Rob didn’t stop her.
“It’s so big!” she whispered, seeing the bulge in his underwear. Jill hooked her fingers into the elastic waistband and drew them down to his knees, allowing his 11” organ to flop out right in front of them both.
“That’s not just big, Jesse, that thing’s fuckin’ HUGE!!” Jill said, awed.
He put one hand on each of their heads, noting the difference in texture. Jesse’s dark hair was coarse and thick, while Jill’s blonde tresses were silky and soft. He pulled Jesse’s face a little closer.
“I want you to go first.” he told her. He felt his cockhead brush her lips. “Open your mouth and suck it, Jesse.” he urged, then felt a delicious warmth as she enclosed her lips around him.
“Ohh, fuck yeah.” he sighed, pulling her face closer. She felt it sliding deeper and deeper into her mouth, then instinctively pulled back, pushing both hands against his hips.
“Not so fast!” she gasped, spitting. “Are you trying to choke me with it ?”
“My turn.” Jill announced. “Let me try.”
Without hesitation, she took it in her hand and popped it in her mouth. She let him push it in, but as it neared the halfway mark, her eyes suddenly grew wide and she, too, pulled her head away.
“It started going down my throat!” she exclaimed. “Nobody could take all that; it’s just too big!!”
“It’s okay, girls, I know you tried your best.” he said. “Don’t worry about finishing. It’s cool.”
“WHAT - THE - FUCK - IS - GOING - ON - HERE!!????!!!” came a voice from the doorway. It was the girls’ mother, Lisa, home from work, and as the three young people stared at her without answering, her anger grew and grew.
“What the fuck are you doing to my daughters?” she demanded, looking straight at Rob. Bright spots burned at both her cheeks.
“He didn’t do anything, Mom. This was all our idea!” Jesse said, quickly jumping to her feet.
“Yeah, we were playing cards, and he won, so we had to… we had to…” Jill volunteered.
“You were betting sex with my daughters?” Lisa demanded, still looking furiously into Rob’s face.
“Mom, that was our idea, too.” Jesse told her. “He only wanted to play for toothpicks, but it was Jill’s idea to play for kisses. And for the second round, it was me who suggested doing bases. You know, first base, second base?”
“Mrs. Miller, I never meant for it to get this far, honest, but every time they lost, they wanted to go another hand and up the stakes.”
“And just how much DID they lose?” Lisa said, still angry, but not as furious anymore. She knew her daughters, and everything they had told her fell well within the boundaries she knew they were capable of. “Tell me the truth!!”
“Well, they both have to give me a blowjob, right now, naked, but I agreed to let them off only being topless for it.” he said. “And, they both lost their virginity to me at come later date.” He paused. “I’ll totally let them out of the sex thing later if either one of them doesn’t feel comfortable going all the way. I’m no rapist.”
“Is that right?” she said. Her eyes finally dropped to his crotch, and her breath caught in her throat at the size of his package. “How… how did they do at… at sucking it?” she asked, breathlessly.
“Umm, well, Jill was able to go down about halfway on it, and Jesse… much less.” he told her. “I was just letting them off the deal, since neither one of them could finish when you came in.”
She looked hard at first Jesse, then Jill. The girls blanched, knowing that look.
“Is that true, girls? Neither one of you could finish?”
“Yeah.” Jesse said, glumly. “It’s true.”
“I tried, Mom, honest I did!” Jill said earnestly. “But it’s just so big! I guess I’m just no good at it.”
“Well, it’s been a long time for me, but some things are never forgotten. Jesse, Jill, come over her. Right next to me, I said!” she ordered, seeing them hesitate. “Watch closely at what I do.”
She looked over at Rob and licked her lips with anticipation.
“Come here, young man. It seems my girls owe you a blowjob, and I’ll be damned if I’m going to let them back out of it and quit before they make you come. Even if I have to show them how myself!”
She went to her knees as Rob approached, taking him in hand. It was only half hard, but she took it in her mouth and sucked on it, letting him twine his fingers through her luxuriously thick, fiery red hair.
He pulled her mouth onto him as both her daughters watched, astonished as she allowed inch after inch to slide between her lips until her nose was pressed tightly into his curly brown pubes.
Jesse and Jill watched in awe and surprise and their mother went to town with his whole thing in her mouth. She was sucking on it, her cheeks hollowing in and out with the force of her tongue working it’s magic against his sensitive underside. They could see her throat moving as she swallowed every few minutes. Obviously, it wasn’t bothering her that she couldn’t breathe, as she bobbed her head up a long minute later, hardly out of breath at all.
She let him go out of her lips with a pop, then turned and smiled at her stunned girls. She licked her lips with relish.
“God damn!” she said, further shocking her kids. Lisa didn’t go to church or anything, but her daughters had never heard her swear, either. “I haven’t tasted cock that good, ever, in my whole life!” She looked up at Rob and smiled at him, her eyes shining. Rob couldn’t answer. He was still trying to wrap his mind around the blowjob this innocent looking mother of two had just given him.
“You see girls, that’s how you do it!” she said, triumphantly. “Jesse, you get down here. You’re first.”
“But, Mom, I already tried, once. It’s too big for me!” she protested, but went to her knees obediently beside her mother.
“But nothing, Missy! You made a bet; you lost the bet, and this family doesn’t have any welshers in it! You will try it again, and you WILL learn to do it the way I just showed you!” her mother snapped at her.
“God know your father didn’t leave us anything, so about the only two things you have to cash in on are your brains and your beauty. You were both lucky to be blessed in both areas, but you have school to teach you about your brains.” she said grimly. “However, it’s going to be up to me to teach you how to use your beauty. Just as brains are a dime a dozen, and only the TRAINED brains are truly valuable, beauty is not rare, either. However, a beautiful TRAINED girl is one of the most precious things to men on the planet.” She looked up at Rob once more. “Isn’t that right, young man?”
“Yes, ma’am.” he agreed hoarsely. “Will you marry me?”
She laughed, a tinkling little sound. “Ask me again in a year. I might take you up on it.” She looked at Jesse and Jill once more.
“You see, girls? I can get proposed to within 30 seconds of having a man’s cock in my mouth, and it’s been 15 years! That’s the power of training! Understand?”
“Yes, mommy.” Jesse whispered contritely. Jill echoed her.
Her voice softened considerably after that.
“Now honey, the thing, you have to relax your throat and let it in.” Lisa told Jesse. “Don’t worry about gagging or not being able to breathe. Just let go and enjoy it!”
Lisa had one hand on Jesse’s head and the other on Rob’s ass, guiding her eldest daughter in her first deep throat maneuver ever. She knew the girl wasn’t going to be able to take the whole thing on her first try, so she allowed her to pull back after taking about half of it.
“Keep sucking on the head it, that’s it, dear. You’re doing just fine.” She let go of Jesse’s hair as Jill knelt down on the other side of her.
“I want to try, Mom.” she said.
Lisa smiled at her. “I just bet you do.”
She looked over a her other daughter, who was licking Rob’s cock all up and down his length. “Okay, Jesse, you can stop now. Your sister wants a turn.”
“So, I just relax and keep sucking on it, right?” Jill asked.
“Basically, yah.” Lisa agreed. “I’m sure if Rob wants you to do something different, he’ll let you know.”
“Why don’t you show her again, Mrs. Miller?” he grinned down at her. She glanced up at him again, smiling, then took him in her mouth once more, maintaining eye contact as she took his whole length. Slowly, she brought her head back, finally allowing it to go with a loud slurping noise.
Jill wasted no time getting it into her mouth, going down on it as far as she could, but found she was having trouble letting it enter her throat, too. She settled for bobbing her head up and down on the half of it she could manage, sucking and laving her tongue on his big cock, much as she had seen her mother doing.
Either she was a good as her mother on the part she was doing, or Rob had just had enough, because just a few minutes after settling into a steady rhythm, Rob grabbed her head and let out a loud, grunting moan.
Jill’s eyes opened wide, and she jerked her head back just in time to catch Rob’s second blast of hot come right on her upper lip. The first big load had gone right into her mouth, some of it jetting right down her throat, as she had been on the downstroke when he erupted, and her throat was halfway into it’s swallow routine anyway.
His third shot out and coated her from forehead to chin with ropy white splatters as he took it in hand and aimed it. He stoked it once and another load of jizz shot out, this time right onto Jesse’s shocked face, about half of it going straight into her mouth, half open in shock at seeing his come on her sister’s face.
Lisa began to laugh at the looks on her daughters faces when his last few spurts were splattering out onto HER forehead, and she quickly took him in her mouth, sucking the last dregs out of his balls.
He looked down at Jesse and Jill stunned expressions and began laughing right along with Lisa.
“Haha, you two look like you didn’t know that was going to happen!” he chuckled.
“I didn’t know there was going to be so MUCH of it!” Jill said, wiping her eye clear where it was glued shut by goopy goo. She swallowed thickly to clear her mouth. “Mom?” she asked. “Will you go get me a towel?”
“No, I most certainly will not.” laughed Lisa. “You two girls are going to lick all of that off each other’s faces and swallow it.” she told them. “That’ll teach to waste it like that!”
“Oh my God!” Jesse freaked. “It’s all over my FACE!!” Her hands were waving in little jerks. “Oh my God!!”
“Jesse, calm down!” Lisa laughed. “It’s not the end of the world.”
“Mom, it went in my MOUTH! I swallowed some of it!! I think I’m going to be sick!”
“Jesse, you stay right here, young lady!”
“Don’t worry, Jesse, you look beautiful!” Rob told her. “There’s nothing sexier than a beautiful girl wearing his come.”
“Really?” she asked, looking up at him, trusting, hoping.
“Oh yes.” he told her. “Unless it’s her eating his come.” He reached down and got a fingerful off her cheek, under her eye, and wiped it into her mouth.
“Gah, yuck, what are you doing?” she cried out. “That’s disgusting!” She spat onto the floor.
“Jesse!” said her mother sharply. “You WILL learn to swallow come, young lady! Never do anything halfway, you understand me?”
“Yes, mother.” Jesse replied, meekly.
“Good! Now bend down there and lick that up off my floor! If I ever see you wasting his precious seed like that again, I’ll.. I’ll…” She came to a stop, too furious to go on. Jesse hurried to obey, slurping the mess of the floor and swallowed it as she sat back up.
“Besides,” Lisa said, her voice all syrupy and honey like again, “I like the taste of it.” She licked a big mouthful off Jesse’s cheek, then passed it to her daughter by kissing her on the mouth.
Rob was watching the kiss, and Jill saw that it had a noticeable effect on him.
“Ohh, Mom, I think he LIKES watching you kiss Jesse.” she giggled with glee. “His thing is getting hard again!”
“Call it what it is, Jill.” Lisa told her. “That’s his cock. Those are his balls. That stuff…” Lisa paused from her pointing and licked a big mouthful off Jill’s lips, then kissed her, too, passing the come with her tongue. She also reached up and caressed both her daughter’s breasts.
Jill returned the kiss with passion, wrapping her arms around her mother and moving her down so that Lisa’s mouth found her nipple.
“Oh, yeah, he REALLY likes THAT!!” Jesse smiled. “Look! It’s all the way hard Kiss me again, mother!”
“No, Jesse, you kiss Jill this time. I believe your mother told you two to lick each other off, right? Well, just because I’m here and we’re doing this doesn’t mean you don’t have to listen to your Mother, you know. You still have to obey her.”
He looked down at Lisa and held out his hand to help her up.
“Mrs. Miller, shall we go over to the couch?”
“Call me Lisa.” she said, allowing him to help her up. “I’m only thirty four.” she said. “When you call me Mrs. Miller, it makes me feel old.”
He didn’t reply; he just took her in his arms and nuzzled her neck as he opened the buttons on her jacket.
“Ohh, God.” she sighed as he pushed the dark material off her shoulders. She let her arms dangle at her sides, and the jacket fell to the floor and he kissed her neck and licked her lightly behind her ear. His strong arms were nearly holding her up, and then she was being lowered to the couch.
As he slid his arms out from behind her, he smoothly brought them to the bottom buttons of her blouse. He gently pulled it out of her skirt and began unfastening them, one at a time. He licked his come off her forehead with one broad swipe of his tongue and fed it to her with hs tongue, letting them dance together.
“Ohh, mmmmph!” she moaned in protest as her shirt fell open completely and he began palming her breasts through her dainty lace bra.
“What’s wrong?” he smiled at her, sliding his hands off her and supporting himself on his arms, at either side of her shoulders.
“I can’t… we can’t!” she said, her voice catching on a sob.
“Why not?” he asked. “You want this!”
“No, please, let me up!” she begged.
“Lisa, I’m not holding you down.” he told her, looking steadily into her eyes.
“Rob, I can’t… not with you, not with anyone!” she said, looking away. “I promised Jason…”
