Teaching Daughter Self Esteem Ch. 05

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My daughter and her girlfriend ask Daddy for dating advice.
4.3k words
4.67
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Part 5 of the 15 part series

Updated 06/07/2023
Created 01/15/2014
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dannyboy111
dannyboy111
4,556 Followers

That Friday night Elaine had to work late doing inventory. Several years earlier, it seemed, the chief financial officer of her company had successfully embezzled a big hunk of the company's funds, and was now living it up in one of those tropical mosquito-filled paradises that are too backward to have effective extradition treaties. The company, meanwhile, had to go into receivership, and one of the conditions imposed by the court and shareholders was that every year they had to undergo the most strenuous inventory check that had ever been devised. Every box had to be opened, every paper clip counted, every mousetrap in the warehouse classified as to what type of cheese it contained. Granted, it was mainly an exercise in closing the barn door after the livestock had already escaped, but given the scope of what had happened you could kind of sympathize with the creditors and shareholders who had been left holding the bag.

To their credit, the management -- many of whom had been replaced after the scandal -- tried to make the best of an embarrassing and largely useless annual exercise. They dubbed the inventory check the "Annual Paperclip Hunt", encouraged employees to bring dishes for a potluck dinner, and even hid a prize of a hundred dollars in an envelope somewhere in the warehouse for a lucky corporate drone to find each year. And everyone got time and a half overtime for the extra hours they were forced to work that day.

So Elaine was gone that Friday night, with no idea when the Paperclip Hunt would end and she would get to go home.

Katie, meanwhile, had a typical Friday night planned. While other teenage girls primped for dates, Katie and her friend Randi got together as fellow self-imposed outcasts. Friday nights frequently included watching a movie with Elaine and me, but more often the two of them hung out in Katie's room together, cruising internet sites or chatting with each other.

Elaine and I were disappointed, naturally, that Katie never went out on dates, but by this time we were used to it. We were grateful that at least she had such a close friend in Randi.

The two were like sisters. Temperamentally, they were so completely in synch that they occasionally finished each other's sentences when we spoke during the many dinners that Randi shared with our family. Physically, on the other hand, they were quite different. Katie was blonde haired and, as we had recently discovered, had a rack that almost defied belief, especially given her short, lithe dancer's body. Randi, on the other hand, was half Japanese, with the long, silky black hair that Asian women sometimes have. The combination of her Japanese mother and Irish-American father had given her pale white skin that contrasted beautifully with her jet black hair. As for her figure, though, I had no idea, given that she, like my daughter, was given to wearing shapeless, drab oversized clothing designed to hide her figure and help her avoid being noticed. She and Katie were the two shyest people I think I have ever met.

That night, with Elaine gone and me tired from work, I threw together a quick marinara sauce and the three of us ate pasta together. At dinner I allowed both girls to have a glass of wine with dinner. I figured that they were both 18 and adults; given their social inexperience they were more excited by the idea of me allowing them a glass than I think most 18 year olds would be. But I figured that this, too, was a harmless way to carry out Elaine's and my project of gradually bringing our daughter out of her shell and into the world around her.

After dinner, I settled down with a mystery novel while Katie and Randi went off to Katie's room together. Down the hall I could hear them giggling together over some conversation or other. Meanwhile, I immersed myself in my book, one of those English drawing room mysteries in which the butler -- honest to God, the butler! -- was a main suspect.

A half hour into my reading -- by this time I was sure it was the butler -- I heard a crash in Katie's room. It sounded like breaking glass. I put down my book and walked down the hall.

I knocked on the door and, without waiting for a reply, rashly opened the door. Inside, I found Katie and Randi both on their knees picking up broken glass. On the desk by her bed I saw the wine bottle and one glass. It appeared that the two girls had taken the bottle and both their glasses into her room, then had knocked over one of the glasses. It wasn't a big deal, really.

What WAS a big deal was the way that they were dressed. Katie was picking up glass shards while dressed in her old green nightie, the one she'd outgrown but still liked to wear. With her facing away from me while she searched the carpet on her hands and knees, the nightie rose up so high that it revealed the perfect globes of her tight round ass.

Randi was even more striking. For once, I could see she had shed the innumerable layers of clothing that she wore as camouflage, and was instead dressed in a flimsy button-down blouse all of whose buttons were undone except one near the bottom.

And that was it. No bra, no pants or skirt, no underwear.

For the first time in several years, I had a chance to see Randi's figure. It was stunning. Her slim arms and legs looked gorgeous in the golden light of Katie's bed lamp. Her waist and ass were small but tight. Being half Japanese, there was no way she could be as well-endowed as Katie, but her Dad's Irish genes must have had a pretty big influence. I would estimate that her tits were a C-cup size. It was amazing to see an Asian girl with such full tits.

"What's going on?" I asked.

"Oh, Mr. J!" cried Randi, using the nickname that she'd adopted for me several years ago. "Katie and I were just. . . ."

"You were drinking wine in your bedroom," I said sternly.

"Yes, Daddy," said Katie sheepishly.

"And what else were you up to?"

"We were talking about boys, Mr. J."

I could tell there was something more to it. "And what else?" I asked.

"We were . . . um. . . ."

"Come on. Out with it."

"We were practicing," said Katie.

"Practicing what?" I asked, mystified.

"Practicing kissing," Katie said.

I looked over at Randi, her nearly bare tits showing through her sheer white blouse, then over at Katie, whose humongous tits were stretching her poor old nightie almost to the point of tearing the threadbare cotton. "Why in the world would you do that?" I asked.

"Well, you know . . ." said Katie.

". . . it was in case a guy should, like . . ." continued Randi.

"Like, ask one of us out, you know?" said Katie, finishing the girls' thought.

My cock started to get hard as their words sank in. "Show me," I said.

"Right here?" asked Katie.

"Right now?" asked Randi.

"Come into the living room," I instructed them.

I made a quick check of the carpet to make sure Katie had indeed cleaned up all of the glass fragments, then grabbed the wine bottle and remaining glass and followed the two girls into the living room. They sat on the couch together facing me.

"Okay," I said, "Let me see what you were doing."

Randi tentatively bent forward and pecked Katie on the lips, her eyes on me the whole time. She was clearly afraid of a negative reaction on my part. I knew that her parents, though divorced, were both pretty strict and protective. I guessed that she was afraid I might call them and tell them what she and Katie had been up to, leading to God knows what reaction on their part.

"Is that all you were doing?" I asked. I crouched down on the ground to be at their eye level, then laid my hand gently on Randi's arm and caressed her forearm lightly in reassurance. "Don't worry, sweetie. I'm not angry, and I promise all of this will stay between us. Now -- is that all you were doing?"

"No, Mr. J."

"Okay, then, show me the rest."

Randi leaned forward again and kissed my daughter -- much more intensely this time, though even now I sensed that this might only be a prelude.

Katie, true to her hesitant, shy nature, kissed her friend back, but her heart was only half in it. She was self-conscious at being caught in such an activity and afraid of a negative reaction from me.

I bent forward and brought my fingertips to my daughter's cheek. She turned and looked at me.

"Is that it?" I asked. "Is that all kissing is to you?" Katie blushed. "Think of Rhett Butler and Scarlett O'Hara in 'Gone With the Wind'. Think of those two people rolling in the waves in 'From Here to Eternity'." I smiled at both of them. "Is that all you've got?"

Randi smiled at me, finally relaxing. "How's this, Mr. J?" she asked. She reached over and took a gulp of wine to bolster her courage. Then she leaned in to Katie and put both her hands on Katie's two cheeks and gave her a soulful kiss with what looked like a lot of tongue action. Several seconds later, the girls split apart and both looked to me for a response.

"Not bad," I said, a smile on my face. This was getting better and better. "Try it again, and this time I want you to really put your heart in it."

When they kissed this time, I could see much more passion on both sides. I gently reached forward and brushed the hair away from the side of each girl's face so that I could have a better view. My heart was pounding in anticipation of what I hoped would come soon.

When they broke apart this time, I put my hands on both their thighs. "That's very good. I'm sure you're going to be very good kissers some day when you start going out with boys. But in the meantime, I think you're right to practice."

I sat down on the couch between my daughter and her best friend. "Let's try it again, shall we, Randi?" I said, then bent forward and began kissing her. I started slowly, caressing her outer lips with the tip of my tongue, and only gradually moved my tongue farther in. By the time I was all the way in, Randi was moaning into my mouth.

When we both came up for air, I asked, "How was that, sweetie?"

Randi smiled dreamily. "Really nice, Mr. J. Let's do it again!"

"Not yet," I admonished. "It's Katie's turn."

I spent the next ten minutes going from one to the other, my busty blonde daughter on one side, and her svelte, scantily clad, nearly nude Asian girlfriend on the other, kissing each one deeper and deeper. It quickly reached the point that while I was kissing one girl, the other was anxiously panting and sidling even closer to me, anxious for her turn to start. When one was kissing me, the other was often taking a sip of wine or reaching around me, hugging me from behind and kissing my neck. Sometimes I encouraged the two increasingly tipsy and horny girls to reach over my body and kiss each other while I watched -- for more practice, of course. While they kissed each other, I stroked their hair and necks, whispering encouragement. "Give it everything you've got," I urged. "More! More!" I leaned in and embraced both girls as they kissed, my hand roaming up and down their backs and all the way to their perfect soft round asses.

It was obvious through it all, though, that Randi had a somewhat different agenda than Katie did. Randi enjoyed kissing me a lot, but I could see that she enjoyed kissing my daughter even more. I was beginning to suspect that under that lovely little alabaster Japanese body, my daughter's best friend might be a lesbian with the hots for her.

After several minutes of making out together, I said, "Of course, kissing is only a part of dating. When you kiss your date, you should be prepared for more than just that."

Katie looked at me anxiously. "Are guys going to expect me to . . .?"

"Let's just take it slowly," I said, soothing her.

Katie took another sip of wine and, giggling, reached over to Randi. Cupping one hand behind the back of Randi's neck, Katie brought the wine glass to her friend's lips and tilted it to the other girl's lips. Randi let my daughter pour the liquor down her throat. Then, laughing, she took the glass from my daughter's hand and returned the favor, cradling Katie's head with one hand and tilting the glass toward Katie's lips and encouraging her to drink more. Meanwhile, I sat back between them, stroking their backs and smiling approvingly. It was doubly erotic to watch the two half-dressed girls encourage each other to get drunker. My cock was as hard as an iron bar. A little of the red wine dribbled down Katie's chin and onto her green nightie. She giggled some more and swayed slightly in her seat. The wine was having an effect.

"Oh, honey!" I said, soothingly, "Watch out that you don't stain your nightgown." I took the bottom hem in my hands and pulled the nightie off over her head, exposing her luscious, gravity-defying big tits and leaving her dressed only in a thin panty.

She gave me a drunken smile. "Thank you, Daddy," she said. In what appeared to be an unconscious move, my daughter responded to the physical sensation of having her oversized tits freed from the restrictive clothing by cupping and caressing her tits briefly. The effect, looking at her, was as if she were presenting them to me as gifts for me alone.

Returning to the subject of dating, I said, "Boys are likely to want to feel your breasts, I think." Then I turned to Randi and undid the last button on her blouse, fully revealing her surprisingly well-endowed breasts and her beautiful, flawless pale skin. I started to play with her lovely young tits. "Do you think you would like that, sweetie?"

"I . . . I guess I would," said Randi, biting her lip while I tweaked her nipples and pecked at her lips. "And if he's doing that, am I supposed to just sit here and let him?"

"I guess that depends on you," I said evenly. "If you don't like it, you should tell him to stop." I paused a moment and kissed Randi some more, tasting the wine on her tongue. "On the other hand, if you like it, you need to show him that you do -- that you're not passive or frigid."

"How. . .?"

"You should put your hand right here," I said, placing her hand on my hard cock.

I turned to Katie. "You too, sweetie. Show your date that you like him. When he kisses you, show him you appreciate him." I pulled her hand to my crotch, so that now both girls were caressing my cock and balls through my pants.

"Good girls," I said. "You're both learning really quickly. Now, Katie, you undo my belt while I kiss your friend."

A minute later, I had definitely reached heaven. My pants were pooled at the floor around my ankles, while my two girls cooperated in stroking my shaft, my balls and my cock head. Meanwhile, I had both my arms around the two girls pulling them to me, and I alternated between kissing first one, then the other. "Am I doing it right, Daddy?" Katie asked breathlessly between kisses and more sips of wine.

By this time, Randi was being swept along to a place I don't think she had expected to go. She seemed especially taken aback when she broke apart after one of our kisses to find that her friend, my daughter, had gone the next step and was bent forward with my dick in her mouth while I had been kissing Randi. To overcome her hesitation and not give her time to think, I pulled Randi's face back to mine and kissed her harder, while my other hand pushed my daughter's face deeper onto my hard cock.

I broke off my kiss with Randi for a moment. With my hand guiding the back of my daughter's head up and down, up and down, I looked into Randi's deer-in-the-headlights eyes. I think my grin must have stretched from ear to ear as I said, as matter of factly as I could, "It looks as if Katie has skipped to the next lesson: if you really like your date, you should show your appreciation by sucking his cock. See how easy it is? See how much Katie likes showing her appreciation?" Then I went back to kissing my daughter's increasingly horny Asian girlfriend and groping her ripe tits.

I was finally where I wanted to be: my big titted blonde daughter was sucking my cock while her slim, sexy Japanese girlfriend was kissing me as hard as she could, desperate in her inebriated state to prove that she knew how to treat a grownup man. The hand that had been on the back of my daughter's head urging her to suck deeper now drifted lower, and I cupped one of her humongous breasts. Tweaking her nipples caused her to gasp in orgasmic shock even through her horny slurping of my cock.

That was about the time that Elaine came home from work. I have no idea how long she had been standing in the middle of the room watching us. All I knew was that at one point I looked up from kissing Randi and saw my wife only a few feet away, standing with arms folded as she watched.

When she saw that I had finally noticed her, she simply smiled ambiguously and said dryly, "Hi, honey, I'm home."

Katie lifted her mouth off my cock with a loud pop, while Randi jerked in surprise and fear.

I put a blase face on it, saying simply, "Oh, hi Elaine. The girls and I were talking about boys and dates and . . ."

". . . doing a little show and tell?"

"Something like that." I smiled. I put my arms around both their waists and cupped their tits, showing them off to my wife by hefting them from below and jiggling them for Elaine's benefit. I knew exactly what I looked like to Elaine, brazenly fondling two nearly naked, drunken and submissive girls' tits while my erect cock stood up from my crotch, twitching and begging to be played with, displaying to my wife exactly where things were going. "They said they wanted to practice how to deal with boys in case they get asked out on dates," I said, tweaking both girls' nipples. Katie and Randi both jumped in their seats at the sensation. I hugged them even tighter and the possessive smile I directed at my wife got even wider.

"I think these young ladies need a lot of guidance," I said, squeezing their tits again and pulling them closer as the three of us sat on the couch facing my wife. My cock, which seemed so hard before, felt even harder now that I knew my wife was watching us. I ached for my two teen sex students to put their hands back where they belonged -- on my cock and balls. So I said, "Girls, why don't you demonstrate what we talked about -- how to show a man that you appreciate him?" First Katie, then Randi tentatively each wrapped a hand around my shaft and started stroking me slowly up and down. They both looked up at Elaine uncertainly seeking her approval.

"Good girls," I said. I looked back at Elaine and added, "They're learning really well." With my hands still wrapped around the girls' waists and cupping each of the girls' tits, I bounced their big soft tits up and down, showing off my control of these compliant teens and beaming at Elaine the whole time. The girls' hands rose up and down on my cock.

Elaine put her purse and car keys on the table as if what she'd walked in on was merely a day in the life. "I see," she said, as she watched her daughter and her daughter's friend being fondled by me while they stroked my hard dick. "Mind if I get a glass of wine?"

"Sure," I said. "The bottle's right here."

Elaine looked at the wine bottle, which was mostly empty by this time, and gave a crooked smile. She looked from one girl to another, assessing how drunk they were. "Of course it is. I'll just be a moment."

A minute later she was back in the living room with an empty glass in her hand and she began pouring herself some liquor from the bottle. It looked as if she had taken a moment while outside the living room to remove her bra, then re-button her blouse most, but not all of the way. "Can you make some room for me on the couch?" she asked.

She sat down on the other side of Randi. "Randi, sweetie," she said, "why don't you show me what you've been learning."

"Um, gosh Mrs. J. . ."

"It's fine, Randi dear." She put her hand on Randi's cheek and began gently drawing the innocent teen toward her face. "Show me how well you can kiss."

dannyboy111
dannyboy111
4,556 Followers
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