How Can I Help - Caitlin

Jack looked at his friend wondering if he'd just won the lottery but dismissed it as Dave had never strayed from his marital vows, never went to strip clubs with the guys, never flirted with waitresses or barmaids. 'Too bad,' he thought, 'this is going to be a frustrating night.' On the other hand, as much as he preferred feeling warm soft flesh against his body when he came, this would make jerking off about as hot as it gets.

"Girls, if you want to have a drink I'll allow it. I'm getting a beer. Jack? what are you having?" Dave said.

Grace had a beer and Caitlin asked for a gin and tonic. Then they went downstairs to the den where the poker table was staged.

Dave and Jack laid out the basic rules and strategies. When to fold, when to draw, how many cards to take, etc. The girls listened, Caitlin jotting down notes, and Grace nodding.

"Then there are the tells," Dave said.

"Tells?" Caitlin looked up from her notepad. "What are tells?"

Jack smiled, "Body language, facial expressions that give away what you're holding, or more exactly how you feel about your hand." He took five cards, looked and them then slumped back in his seat. Even though his facial expression didn't change, the three knew his hand was crap.

"You don't need to be stony, just need to be consistent." Dave took five cards, glanced at them then took a sip of his drink. He glanced around the table as if expecting the betting to open.

They each got their $20 in chips and they started. At first, the two girls gave away their hands, either with a quick smile or frown but after losing half their stakes they focused on not reacting. It was a lot harder than they thought.

Jack was piling up the chips and within an hour he was up $40. He slid $1 into the pot looking at Grace's meager pile of chips. "You're going to be out if the bidding gets too high. Did you bring more cash?"

Grace shook her head. She couldn't believe how many times she had good cards which won the pot but it was meager. "I'm trying to keep still...a straight face but I obviously still have a tell," she sighed.

Dave chuckled and pointed to her chest, "Your nipples. When you were dealt the three aces, they must have popped out an inch," he chuckled.

"Then that's not fair," she moaned, "unless I wear a padded bra..."

Jack shook his head, "Please don't, it evens out." He pointed to the small pile of chips in front of his host. "I know for a fact Dave's played tons better in the past...seen him wipe everyone out but I think your tits are a great distraction." He looked at Caitlin's tits and grinned, "Poor guy. I've seen him look at his daughter's tits also. Next time you guys play poker perhaps the padded bra thing would be a good idea...but I'm not complaining."

Grace smiled, "at least having a bra would make strip poker better...more layers." She looked at her meager chips, "Speaking of which, you think my shoes are worth $5?"

"Hang on, if this is going where I think it is...how old are you?" he asked. "Both of you."

"18," both girls said.

Jack looked at Dave, "You vouch for Caitlin being 18? OK, Grace, show me an ID. You look 18, very much look 18," he said as he admired her chest, "but a guy needs to be sure."

Grace got up and went over to get her bag. She reached inside, pulled out her wallet, and came back over. "See? 18 and 7 months."

Jack looked at her license and nodded. He then looked at his friend who was smiling, "Sure. We can do $5 per item...shoes, socks, shorts...ahhh, yesssss. I like this game."

Caitlin sighed, "Damn! Ok." She took her shoes off and tossed them aside to join her friends.

Their fortunes didn't change much and Jack grinned at his friend as Caitlin stood and slid her shorts off her ass and down her legs. He was surprised to see the girl was wearing a thong having assumed she was more uptight than that...but not complaining.

Caitlin blushed seeing all three pairs of eyes trying to see as much of her privates as possible and before she could sit and hide her father spoke.

"While you're up, Jack and I need another beer. Grace, would you like one?" Dave asked.

Caitlin groaned and blushed more but quickly trotted into the kitchen to get the drinks. She was able to carry all four in her hands but any chance of modestly covering her barely covered pussy was out of the question.

Then to make it worse, when she got to the table Grace traced a finger up her slit and smiled at the guys, "I made sure she was shaved here this afternoon."

Caitlin couldn't swat her hand away as she was handing out the drinks, but when she finished, she plopped back into her seat.

Jack looked at his friend and smiled. Dave wasn't as virtuous as he let on. He was staring at that clearly defined cleft while unconsciously licking his lips.

The next few hands went as the ones before had gone and the men sat back eagerly watching as both girls peeled off their thongs now sitting just in their small tops. There were no more obvious tells as both girls' nipples were perpetually rock hard. They were able to rally a bit but inevitably around 11 PM, both girls had just one more item each to cash in.

Grace stood up without a word and pulled the tight tee up and over her head, tossing it onto the pile of clothes. She rubbed her breasts as if the tight top restricted blood flow then smiled, "I guess this is more like how my previous poker games ended up." She looked at Caitlin, "I guess your Daddy is going to get a look at your boobs."

The redhead blushed, standing slowly. She remembered both men's eyes on her red bush earlier almost feeling their gaze touching her there. She pulled off her top and then tossed it behind her. Rather than sitting down, she let the men get a good look which surprised her. She'd always had these dreams she was naked in front of a large group and couldn't find anywhere to hide but this was the opposite. The looks on all three were admiring. "I guess this is our last chance to rally, " she said softly before sitting down.

There was no rally and Grace internally groaned seeing her two pair, aces over kings. Possibilities were going through her head but only one seemed probable. She asked to put in an IOU but that was shot down

Jack had slid 1$ into the pot a smile on his face seeing no chips left in front of the incredibly sexy girl. He sat back, "What else do you have to offer?" he smiled.

Grace sighed, "Nothing. I'm out of clothes."

Jack looked over at his friend, "I could use a blowjob. That would get you another $5."

"$5! I'm better than that! I'd do it for $50," the cute blonde sputtered.

Jack nodded, "I'm sure, but let's talk about leverage. You want to stay in with...what do you have? Two pair? Three of a kind?" he said nodding at her cards, "$5 and I'll not drop...neither will Dave and if you win the hand it'd make up for the insulting offer."

"Ok...shit. Let's play out this hand. Wait, does that mean I have to suck both your cocks for $5?" she asked looking at both men.

Dave shook his head, "That would be unfair, and had I spoken first..."

Grace nodded and got her chips. They played, all stayed in and she won her first big pot of the night...$28! She felt a rush as she pulled the large pile towards her. "Finally! Ok, I'll make good on my deal but if you ever tell anyone I sucked your cock for five bucks I'll rip your balls off," she sighed. She got up and stood in front of the good-looking man in his mid-fifties. She'd never been with a guy over 25 before and she was curious if an old guy like this had as much grey hair between his legs as he had on his head. She knelt, unzipped his pants, and pulled them down as he lifted his hips.

Caitlin was looking over curious to see how differently Grace sucked cock. Her Daddy was also leaning forward, though she thought his eyes were looking at the girl's naked body. Grace was able to take the man's entire cock into her throat without working up to it. She wished she could do that but maybe that's something that comes over time.

Grace was pleased the man was hard...rock hard and leaking copious amounts of precum. There were some fine strands of grey hair but nothing like the amount Jack had on his head. She stroked him and looked up at him, "this is the current definition of a two-bit whore. $5," she sighed. She then licked from his ballsack to the head.

Jack smiled, "Any other time...I'd pay you $500 for the night," he said.

Grace looked at him, "That sounds a lot better..." She opened her mouth and plunged onto the 7" shaft. She knew she was good and though she'd never had one of her boyfriends pay a cent, something was arousing about being bought...even for $5. She knew he was kidding but had no doubt what she'd say if he called her.

Jack grabbed a huge tit and moaned softly. He looked over at his friend, "Sorry, Dave, she's good. Worth every penny," he smiled. "Too bad Caitlin's your daughter, but that's just going a bit too far, even for me...though she's not my daughter...."

Cailin looked at her father and smiled, "Yes, Daddy. Sucking your cock would be wrong...so wrong. Especially if you came in my mouth and I swallowed," she said softly. She glanced over at Jack who had a look on his face that made her whole body shiver.

Jack put his head back as the girl deep-throated him while playing with his balls. He knew he wasn't going to last having been hard for the past hour and a half and the girl had considerable skills. He was thinking it would be worth the $500 to fuck her at another time. If she's this good with her mouth, what are her other skills? He loved women who had lush soft bodies and Grace had all the things that made his blood pressure rise.

Dave was idly shuffling the cards to keep from playing with his throbbing cock as he admired Grace's full body. Caitlin did look just as hot, if not hotter. Her mouth was partly open and her pink tongue was delicately licking her lips as she watched her friend, but it was her tits that made his cock ache even more. Her chest was flushed above, her creamy full tits were capped with pale-pink puffy nipples, and watching her chest rise and fall was mesmerizing. He'd read erotic stories where the girl's 'chest was heaving,' and now he couldn't think of a better phrase. Too bad her friend was staying over...no way would he get relief unless he took care of it himself.

Jack had been getting more and more aroused as the evening went on and nothing he thought of could delay the inevitable. "Fuck, I'm going to cum...oh, shit!" he spat as he felt the peaking in his balls.

Grace groaned as the first hot spurt splashed against the back of her throat. Jack had a lot of cum for an old guy. She had wondered if sperm production went down with age but she had to swallow copious amounts of his tangy cum. She pulled off and wiped her mouth, "You got the better part of the deal," she sighed, "$5."

Jack nodded, "Hey, leverage. I was thinking about talking you down to $1, but you're right, that was a $100 blowjob." He pulled up his pants and looked at his watch. Dave, I need to head back to the wife. Girls, it was nice seeing you...very nice," he grinned as he scanned each. Then he pulled Grace to her feet, "Next weekend Sue is out of town. I wasn't kidding about the $500." He hugged the naked girl, his hands freely exploring her creamy body.

Grace smiled and picked up her phone, "Give me your number and I'll share my contact information."

After Jack left, Caitlin slapped her friend's ass, "You little whore. $500. Shit, how can I get in on that?" Then she looked at her Daddy, "Sorry, Dad. I was joking. You know I'd never..."

Dave chuckled, "I wouldn't tell your mother but it sure would help the finances if you pulled your weight around here."

The two girls looked at their clothes tossed behind where Jack was sitting. "Um, Daddy can we get dressed?" Caitlin asked.

"I should say no but...yeah. I'll see you both in the morning," Dave said as he stood and headed upstairs.

* * *

The two girls finished getting ready and flopped onto Caitlin's bed. Caitlin looked at her friend, "How was Jack's cock? Was he as hard as high school boys' cocks? Not that I've ever felt one..."

"Not quite, but he was very well-endowed. What surprised me was how much cum I had to swallow. I always thought guys lose sperm as they get older. Maybe he used to fill up a cup when he was 18," she wondered aloud.

"You really going to go over to his house next weekend, I mean fuck him for $500?" Caitlin asked.

Grace shrugged, "Why not? I go out with Carl, get dinner, and if I'm lucky a movie out of it. Why not get some serious spending money for doing the same thing?" She thought about something, "I'll need to find out which night. I'll have to cancel my date with Derek or Carl," she sighed.

They talked a bit more then Caitlin had a thought, "You know. I feel bad. I always kiss my mom and dad goodnight. I know Mom's not here, but..."

"I agree, It would be the nice thing to do," Grace said as she rolled off the bad. She was wearing a thin tee and her thong.

Caitlin looked at what she was wearing, "Should we at least put on a robe?"

Grace laughed, "He's seen up both naked. This is almost a nun's habit compared to how we were an hour ago. Come on, I hope he's jerking off. That would be fun!" she giggled. She looked at her friend, "Get ready to need therapy. Seeing your Daddy's hard cock might be traumatic...though it wouldn't bother me."

Dave was reading trying not to succumb to the urge to jerk off. He'd not jerked off in weeks ever since Caitlin offered to take over the 'chore' of sucking his cock. He much preferred her mouth to his hand. He looked over hearing the soft tapping on the bedroom door. "Come in," he said.

He was surprised both Caitlin and Grace came in looking arousingly hot. Both girls had skimpy thongs on and their nipples were clearly visible through the old tee shirts. "What's up? Need something?" he asked as he sat up.

"Just that I never got my kiss goodnight, Daddy," Caitlin said as she came over.

"Yes...Daddy," Grace said, "I never got my kiss either."

Dave thought Caitlin would do the usual peck on his lips but he responded to her tongue and open mouth. He wondered what Grace was thinking seeing her friend passionately kiss her father but then he felt his covers getting pulled down.

"Nice!" Grace said as she pulled out the man's hard cock, "You keep him busy while I take care of this," she sighed.

Dave felt the girl's soft hands replaced with her mouth. He had been gently stroking his daughter's back but with her tongue deep in his mouth, he pulled off her shirt and then grabbed her luscious tits.

Grace was kneeling between his legs looking up as Caitlin's father was groping his daughter. 'This is so fucking hot! Why didn't I bring my phone?' she wondered. Then she saw Dave's hand slide into the girls' thong causing Caitlin to moan loudly. 'Damn! That girl is horny,' she thought hearing the squelching sound of the man's fat finger pumping into her sopping pussy.

Caitlin had never felt anything like this. Her nipple burned under his rough hand but his finger driving inside her and grinding against her clit was amazing. Then she felt hands on her ass.

Grace quit sucking on Dave's cock and reached up and pulled her friend's thong off. "Come here. I was going to have this great cock inside me, but you need it more than I," she said.

Caitlin was in a haze as she let herself be lowered onto her father's hard cock. Her Dad was watching intently, almost eagerly at her as she gripped his cock and slid it up and down her wet slit. She'd watched enough videos to know what to do. She plunged and cried out, bending her head back as she felt her first cock bury itself fully inside her.

Dave was still gripping her huge tits and was now using them to help pace the girl as she bounced on his cock. In the back of his mind, he thought this was wrong, that she should have a condom on but these thoughts only made it hotter.

Caitlin leaned into her Daddy'd hands as she rapidly pounded her ass on his cock. This felt so good that she wondered what took her so long. Then as Grace started kissing her ass cheeks, she leaned over more and kissed her father again. "Mmmmmmm, mmmmmm," she moaned as she felt what her Daddy had been feeling. Grace's tongue on her ass...in her ass felt incredible.

Dave was trying to quell the aching in his balls when he noticed the mirror of Marjorie's dresser. Grace's face was buried between Caitlin's ass and she was obviously tonguing his daughter's anus. He couldn't hold back and tried to push his daughter off but she was thrusting hard against him..Caitlin both heard and felt her father's sperm shoot deep into her unprotected womb. She was so close to her first orgasm but she couldn't quite trigger it.

Grace moved to lick Dave's balls and slick shaft as he came and then sat back as he went limp. Caitlin was still humping his softening cock so Grace gently pulled her off and laid her on her back. She planted her mouth on the cute redhead's pussy, lapping up her father's cum as it leaked out.

Dave looked over feeling his cock throbbing back to life and then sucked on one of his daughter's nipples. Caitlin was grunting loudly and writhing, her face and chest bright red, her legs spread wide. Then he looked at Grace's plump ass and climbed off the bed, opened the girl's legs, laid on top of her, and drove his cock into her pussy.

Grace grunted as the man's fat cock slid deep inside her. 'Impressive! He might be 40 something but he recovered like an 18-year-old,' she thought. She loved this position. It always seemed like the guy's cock was bigger, longer when she was on her stomach. Dave's cum was almost all cleaned out and now she was lapping up the girl's juices. Caitlin's pussy was the sweetest she'd tasted.

Cailin was getting closer and closer wondering if something didn't break soon would she have a permanent injury? Grace was expertly hitting her clit but it was the sight of her father's slick shaft driving into her friend's pussy...or was it her ass? Whichever it, was that was the trigger she needed. "Oh! Oh my....fuck!" she spat as the agonizing ache in her womb just exploded. Her ass was off the bed, her pussy grinding against Grace's face and she was pulling on her nipples. She felt an added rush that she was no longer a virgin and she was having an orgasm for the first time...first of many...she thought.

Grace looked up at her friend after she writhed for a full minute with a huge smile on her glistening face. "Told you. Nothing better in the world." She looked back at Dave, "You can fuck my ass if you like," she smiled, "Got lube?"

Caitlin rolled over and kissed her friend as her father came back and prepared Grace's ass. When Dave pulled the girl's ass up, Caitlin crawled under and watched her father's cock slowly press against Grace's anus. Then she could almost hear the pop as he plunged in. She planted her mouth onto Grace's now neglected pussy and licked. She never tasted pussy before but had Grace's example to go by. Then she felt her friend's mouth back on her pussy and it felt as wonderful as the first time.

Dave's balls were slapping against his daughter's forehead as she ate out her friend. 'Not the first time,' he thought. How many fathers can claim all that he'd done with his daughter? Strangely enough, it seems to have drawn them closer. Then he looked down at the plump ass as he drove into the young girl's anus.

Caitlin felt dizzy from the incredibly powerful smells. The mixture of cum, sweat, and other odors was intoxicating. She moved up to suck on one of those huge balls and got a better look at the plump shaft slamming into Grace's ass. She licked her pussy again and then moved to Grace's perineum. As soon as she tongued the slick smooth skin the girl cried out she was cumming. Grace had pressed her face against Caitlin's crotch and was making the deepest grunts she'd ever heard. They were almost alien sounding. Then her father groaned that he was cumming.