Dad Cums to the Rescue

When Jude resists putting out on her first date with Billy, things go downhill fast. With no mother to guide her, she turns to Dad for some much needed advice. He quickly realizes that Jude wants more than just answers, she wants somebody to practice on, someone to help get her ready for her next date with Billy. It isn't long before Jude entices him into crossing the line...

This story is a work of fiction, intended for adult readers. All characters are adults, eighteen or older, and unusually horny.

Taylor VanCannon.

*****

I kicked back in the recliner, took a sip of Gentleman Jack, neat, and opened the newspaper to the sports page. The Jack went down smoothly, warming my gullet, as intended. It had been a grueling week. As junior litigation partner, it was my responsibility to meet a filing deadline for our largest corporate client. With a staff of ten, I just barely got it done. Now I could kick back. It would be at least two weeks before arguments, and my schedule was clear. Tomorrow was Saturday, and I already had a morning tee time scheduled.

I heard the squeal of tires in the driveway just as the front door flew open. Jude came in, disheveled, with fire in her eyes. Her white blouse was untucked, blotchy with damp areas, the buttons askew.

"Jude," I said, "Is something--"

"Don't," she interrupted, glaring at me. "Not a fucking word."

Jude came to live with us when she was ten, after her parents perished in a plane crash. It took my wife a long time to get over her brother's death, and it fell to me to become Jude's father. Over time, she came to think of Janice and I as Mom and Dad.

I watched her stomp up the stairs, defiantly.

What the fuck was that all about?

I knew that she had a date with Billy, for dinner and a movie, but here she was, home before seven.

I heard the shower running and music playing. Perhaps this wasn't as bad as it seemed, just a date gone bad. She was eighteen, a year older than most of the other Juniors in her high school class.

When Janice passed unexpectedly after a botched tummy tuck, Jude and I went through a painful adjustment that took its toll on both of us. Jude fell a year behind in school, and I poured myself into my work. It was times like this that brought back a flood of memories of our early dates, of the good days, along with thoughts of what should have been.

Lost in my memories of Janice, an hour had passed before Jude walked down the stairs, her short, athletic figure draped in a bright sundress. Her long dark hair cascaded down her shoulders, framing her cute, perky face. She was the spitting image of her mother, my late sister-in-law.

"Sorry to snap at you, Dad," she said, with no trace of her earlier anger.

"No problem," I replied. "I guess your date didn't work out."

"That's an understatement," she said, raising her voice, a flash of anger returning. "That fucking Billy is such an animal. I don't know what to do."

So much for mellowing out.

Her short fuse left me confused, unsure what she wanted me to do. I felt her pain, but didn't know how to offer her comfort. Then it struck me, Janice and I were her age when we met, and our first date had gone badly. Perhaps that experience would provide some common ground for us.

"You know," I started, "my first date with Janice didn't go too well either."

"Really?" she asked, "you two always seemed so happy."

"True," I answered, "but it didn't start that way. I was an all-star football player; she was a cheerleader. Apparently, she didn't share my expectations for a first date."

She laughed, "You mean that you expected her to put out."

That seemed to break the ice, so I went with it. "Right, but Janice knew how to handle it, how to turn an awkward situation to her advantage. She had this theory that all men were untrained pigs. However, she learned early on that unruly men could be brought around, if you just gave them the right incentives."

"This I've got to hear," she said, pulling up a chair and sitting in front of my recliner, ready to absorb more of my late wife's wisdom.

"I'll tell you what," I said, thoughtfully, "describe what went wrong tonight and I'll tell you how she would have handled it, or at least how she would have handled me."

"Okay," she replied, somewhat skeptical. "It's going to be about sex, and we've never really talked about it. I'm game if you are."

"Shoot," I said, "start with Billy, what's he like?"

"He's nice, a little crude. He and his mother have a ranch out of town where they board horses. He's a cowboy and dresses like one. He's strong... and tall... and dark... and handsome." She laughed at her long drawn out characterization. "Am I really that shallow?"

I joined in her laughter. "Okay, he's the man of your dreams. Now the date," I asked, "what happened?"

"We had some time before dinner, so he drove up the mountain, you know, to one of the secluded spots overlooking the city. He parked his truck, and we... made out. After less than a minute, he grabbed for my... well, you know... he started feeling me up. I wanted tender and gentle, but he was rough and crude. It didn't feel good; in fact, it hurt a little."

I listened intently, genuinely concerned. But my mind was elsewhere, back one of my early dates with Janice. What she just described with Billy sounds a lot like how I behaved back then.

"Do you want me to go on?" she asked, realizing my attention had drifted off.

"Sorry, I can pretty much figure out how your date ended."

"You can?" she asked, surprised.

"Sure, you told him to stop, and he got mad, probably accused you of ruining a good date. Did he demand that you make up for it by jacking him off? Did you feel responsible and agree to do it? From the way you looked when you came in, he made a mess all over your blouse."

"Dad," she said, "he did that on purpose, to humiliate me. What a fucking pig. Anyway, how did you know?"

"You're right about one thing, all men are are capable of being pigs, and I used to be one of them."

She laughed again, relieved to get her story out. "So, what would Mom have done, how would she have handled Billy?"

"With a lot more skill than you did."

"Dad!"

"I'm sorry, that came out wrong. What I meant was that Mom would take that situation and turn it to her advantage. She always had a strategic goal and could find just the right tactics to achieve it."

"I don't understand."

"Think about it, what was your strategic goal for your date with Billy."

"I don't know; it was just a date. Dinner and a movie."

"But you knew that you would make out at some point, didn't you?"

"Yeah, so what?"

"Well, how did you want that to come out? Was your only goal to jack him off?"

"Dad... I never gave it much thought. I just thought I'd go along with whatever Billy wanted."

"Think about it now, if you could do it over, what would you want to happen? What would be your strategic goal?"

"This is kind of awkward," she replied, confused and embarrassed. "Can't you just tell me what my goal should have been."

"Sure," I replied, trying to put her at ease. "Your mom always had one simple rule. Nobody gets off unless she gets off first. She had learned from experience that once you get a guy off, it's over. You're done."

"I see," she replied, after careful thought, "so my goal should have been to get off first, before Billy."

"Good, that's how Janice would have approached it. Have you ever had an orgasm?"

"Dad!" she exclaimed, raising her voice in exasperation.

"I mean on a date," I replied sheepishly, "not from... well... you know..."

"Masturbation," she said, completing my sentence. "Yes Dad, I know all about that. In fact, I just got a little relief in the shower, you know, to calm me down after that fucking disaster with Billy."

Fuck! Was I really going to hear about her masturbation habits?

I could feel a long dormant stirring in my cock. I hadn't dated since Janice passed, suppressing my sexual needs by immersing myself in my work.

"That's the right attitude. You're young and have plenty of time to recover from your mistakes."

"What do you mean mistakes?" she asked, "This was my fault?"

Now I'd stepped in it. "You're being too harsh on yourself. Think of it as a failure to reach your goals, that's all. Something easily corrected."

"Okay, I'm beginning to understand. So, how would Mom have handled it?"

"Let's go through it, step by step. Where did things first go wrong, on your date?"

"When he grabbed my..." she said, letting her words trail off.

"Let's say tits," I said, "in talking about sex, especially with your lover, dirty and nasty is always better. Janice loved to egg me on with her nasty thoughts; it drove me crazy with lust."

"Okay," she replied, more confidently, "he grabbed my tits. It hurt, and I told him to either be gentle or just stop."

"How did that work?"

She looked at him thoughtfully, "Not good, it was all downhill from there."

"Stop, and gentle, are not words Billy will respond to. Remember, he's a pig, only interested in getting into your pants and getting himself off."

"Jeez Dad, you make it sound so hopeless."

"Not at all, you just learn how to channel his needs, to guide him towards fulfilling your goal."

"I have no idea how to do that."

"You start by telling him how much you like the way he is touching your tits."

"That's a complete lie," she replied, indignantly, "won't that just encourage him."

"A little white lie," I said, "a tactic to alter his course of action."

"Yeah, but I'm still not getting it."

"This was Janice's special insight. You can only get him to stop what he is doing by suggesting, or promising, something that he will perceive as better. Think about it, what would be better for him than feeling your tits?"

She thought long and hard. This was not coming easily to her. She looked to me, hoping for some kind of hint, but none was forthcoming. "I don't know, offer to fuck him?" she asked, instantly regretting her response.

Was she still a virgin?

"Well, you're on the right track, but you took too big a leap. You offered too much. So much so, that he probably wouldn't even have believed you. Think smaller, something you're sure that he couldn't resist. Maybe something visual."

"I get it," she said, suddenly animated. "I could offer to flash him my tits."

"Perfect," I said, "and you could do it in such a way that he could see how you like to have your tits handled."

"Dad!" she exclaimed. "That's fucking genius. Why couldn't I think of that?"

"You're learning now," I replied. "After a couple dates, this will all be second nature to you."

"Do you mind if I try it now?" she asked, as though it were a perfectly natural question.

I gulped, did Jude just offer to show me her tits. I mean, not me personally, but to try it out, maybe have me critique her technique.

Observing my quandary, she said, "Don't worry, Dad, I don't mind if you see my tits. Somebody has to be the first see them."

The look of surprise on my face made her giggle. Finally, I said, "If you're comfortable with it, go ahead."

She leaned forward and reached behind, unzipping her sundress and slipping the straps off her shoulder. She was wearing a black pushup bra that barely contained her bulging melons. The edges of her large areolas peeked out, but the opaque fabric hid her nipples. She reached behind and unhooked the bra, easing the straps off her shoulders and letting it drop into her lap.

I gasped. Her breasts were creamy white and considerably larger than Janice's, and much firmer. Funny, I'd never noticed it before. Her nipples were soft and puckered, barely sticking out. I suspected that was about to change.

She smiled at me, "They look good, don't they?"

Wow. Talk about hubris. But she was right; they were beautiful. Should I say something? I needed to deflect the conversation away from me. "Billy won't be able to ignore those beauties."

"Do you think?" she asked, gently cupping her breasts, squeezing them. They were definitely a handful.

My cock was stiffening again, and there was no way I could make any adjustments without her seeing what I was doing. I put my teaching hat back on, to offer her advice. "Yes, but you need to get them out much quicker. He will be impatient, and won't want to wait for you to take so much time getting out of your clothes, especially if you have to get out of the seat to reach behind."

"I've got some tube tops that would just pull down, and a strapless bra that hooks in the front." She pinched her nipples, gently tugging on them until they stiffened.

"Perfect, you don't want to give him time to do any thinking of his own."

"What's next?"

"Let him look until you see his mind wander, then ask him if he wants to suck on them."

"That seems odd. Shouldn't I just tell him to suck my tits? Why make it a question?" She let go of her tits and waited for my explanation.

"Because questions beg to be answered. If you tell him to do something, it will challenge him. You want him to think he is in control. Trust me, he'll be sucking on your tits before he completes his answer." I was thankful that she'd stopped handling her tits, and tried to take my eyes off of them, looking instead at her face. Her lips were full, in contrast to the angular features of her face. Her pearly whites were perfectly straight.

"Okay, then what?"

"Well, you'll have his undivided attention, so it's time to suggest there is more to come. Ask him if sucking on your tits is making him hard."

"Why?"

"It will get him thinking about his cock, and what he has to look forward to. Tell him he is doing a great job on your tits, and you really want to return the favor. That will get him thinking about a blowjob."

"I've never done a blowjob before. I've only jacked guys off."

"You need to expand your repertoire and sucking cock is an essential skill. Janice relished it, or at least she acted like she did."

"I'll think about it. So now that he's thinking about his cock, how is that going to get me off."

"Patience grasshopper," I teased, "you need to turn his attention back to you, to your... crotch."

"You mean my pussy?" she said, teasing him back. "You said nasty was better, right?"

"Good girl," I said, "try telling him your pussy is very wet, and that you want him to check it out for himself."

"Ohhh, you're so bad. Kind of like leading him by the nose."

"More like his cock," I said, laughing, lightening the mood, trying to tamp down my own lust. "He'll probably be rough, just like he was with your tits. Put up with it as long as you can and keep telling him he's doing a great job."

"Okay, but I won't be able to get off if he doesn't do it right."

"So, change his focus again. Tell him you want a taste of your juices. That will grab his attention and get his hand away from your cunt."

"Are you sure that's what Mom would have done?"

"I'm guessing," I said, unsure of myself for the first time. "You've got to be quick on your feet, able to change tactics to reach your goal. I'm thinking that if you get his fingers out of your cunt and into your mouth, you can use your own fingers to move things along. Let him watch you do it, for the shock value."

"I see, so I just have to keep working him until I get off. If I can get him to do it, great, but do it myself if I have to."

"Exactly, it will be hot either way," I replied, proud that she was catching on so quickly. "Keep talking to him, the nastier the better. Make sure he knows when you're getting off, don't leave any room for ambiguity."

Her phone beeped, and she looked down to see the incoming text. A look of disappointment crossed her face as she read the message.

"It's Cindy, they moved my SAT prep to early tomorrow. I have to have to cut this short."

I was relieved. I'm not sure how much more of this I could take. Jude had SATs coming up next week and had scheduled daily prep sessions with her study group. "No problem, I think you've got the general idea on how your next date should go. Let me know if you need any more help."

"What if he doesn't ask me out?" she asked, wistfully.

"You'll have to take the initiative, and it may have to start with an apology."

"No way! He's the one who owes me an apology."

"Come on, Jude, it's just a tactic, don't lose sight of your goal. Just suck it up and make sure you get the date. How won't make a bit of difference once you succeed. Just imagine yourself getting off in his truck."

"You're right, again, and thanks Dad," she replied, "you've been a big help already, and I appreciate you telling me about Mom. That's stuff I never would have figured out by myself." She grabbed her clothes and headed upstairs. Before leaving, she turned, giving me one last eyeful, and said, "Sorry about showing you my... tits... I got a little carried away." Then she was gone.

When I was sure she was gone, I took care of my boner right there in the recliner, quickly blowing my load into a kleenex as I replayed the scene of watching her squeeze those beautiful tits.

*****

I had just poured my third Gentleman Jack when Jude walked through the front door. She broke into a wide grin and said, "It's done."

I gave her a quizzical look, unsure what she was talking about.

"The SATs Dad, that's where I've been today, taking the tests. Don't you remember?"

"Of course I do, Jude," I lied. "How do you think you did?"

"I'm happy," she said, brimming with confidence. "I got to all the questions and didn't have to make many guesses."

"Good, I'm proud of you. Want to join me in a drink, to celebrate your achievement."

"Give me a minute to put my stuff away. I'll be right down."

She bounded down the stairs, excited as ever.

She had changed into a tube top and mini-skirt. Was she planning to continue the lesson I started last week? "How about that drink?" I asked.

"I guess," she replied cautiously. "I've never had a real drink, just a few sips of beer and wine."

I pulled a tumbler off the shelf and poured her a short one. "Cheers," I said, handing her the glass and showing her how to clink them together.

"Whoa," she said, fanning her mouth, "that burns going down." She sat down on the couch, across from my recliner.

"It's sipping whiskey, just take it slowly."

"Okay," she said, taking a small sip. "Did I tell you I have another date with Billy on Friday? Dinner and a movie, same as before."

I chuckled. "Did he make you grovel?" Her glass was empty, so I poured her another short one.

"Yes," she replied, "the prick." The Jack had loosened her tongue, and she kicked her feet up on the couch to get comfortable. In the process, she inadvertently flashed her black panties at me. My mind wandered back to the other day, when she put her tits on display for me.

"I figured he would," I said, "but it'll be worth it, you'll see."

"I know Dad," she replied, somewhat wistfully, "but I'm a little nervous about pulling it off. I mean I really want to, but... I don't know... it's a lot to remember, everything we talked about... and, you know, I've never given a blowjob before. What if I mess it up?"

I laughed again.

Was it even possible for a girl to mess up a blow job, especially with a kid like Billy? Unlikely.

"You'll do just fine," I said, trying to reassure her.

"I don't know," she replied, "maybe I should prepare like I did for the SATs... you know... taking practice tests. Maybe that's what I need before my next date..."

She let her words trail off.

Fuck! Was she looking at me for a study partner? Was this a line I was willing to cross? Goddamn the Jack, it was clouding my thinking.

I said tentatively, "What can I do to help?"

"Oh, Daddy," she replied, enthusiastically, "would you do that for me, help me practice what to do with Billy."