Dating My Daughter – Part 23 (The Best Sex Toy)

Hello ISS readers. I am back with this series. My quick intro. My name is Aafi. This is a fantasy fictional story. I’m a divorced 41-year-old guy who has a beautiful and young daughter, Amy. She just turned 19 and I haven’t seen Amy in almost 10 years. But now she has come down to meet me. So this is what happened next.

Amy and I left to the airport after that exhausting but extremely wonderful sex with Olivia.

The airlines upgraded us to the business class. Amy was happy and was trying to look down the beautiful island through the window.  The air hostess was signaling us to put the seat belt on. To make Amy sit down, I grabbed her right boob and cop a feel.

Me: Honey. Please sit down. Let’s have some boyfriend girlfriend time before we go back to our city.

Amy: Yay! You’re right!

She kissed me on my lips. The air hostess offered us a glass of champagne. She kept her hand on my thigh.

Amy: This is so special.

Me: I’m happy too sweetheart

I kissed her soft lips again. My hand was resting on her soft thigh. I slid my left hand over her shoulder and grabbed her left boob.

Me: Fell free to take a nap, honey.

Amy: Okay, daddy. Cuddle me if I fall asleep?

Me: Of course, honey!

Even I dozed off.

Meanwhile, back at our hometown, Elena and Jen continued to explore their naughty teacher-student relationship. Elena was teaching Jen all about sex. Elena took Jen to a sex shop to explore new things and buy her own sex toy. The building was in a dark place.

Jen: Are you sure this is the right place, Elena? It looks creepy as hell!

Elena: I’m sure of it! Nice butt, by the way!

Jen: Shut up! I’m scared!

Elena: Okay! Okay! No more jokes! Look there it is! Come on, let’s get in.

They found the sex shop and entered.

Elena: Woah, there’s so much stuff in here! In my hometown, adult stores are really small.

Guy: Hi, girls. What can I help you with?

Elena: Hmmm, We’re looking for some dildos for my friend and me.

The guy took out four dildos to show them to the girls. They were all of the different sizes. One was blue color, and the body has an up and down wave-like pattern. It was like an 8-inch size.

There was a huge golden dildo, just like Jen’s mom’s dildo. There’s a purple one with the size even bigger than the golden one. And the last one looked like a butt plug which was in black color.

Elena: Here Jen look, I guess we know where your mom got hers from!

Jen: Haha, well, I guess we do. I can’t believe how big it is.

Elena: The purple one looks even bigger! Wow, anal beads. I’ve never tried those.

Jen: Haha, what kind of teacher are you? You haven’t tried everything yet.

Elena: Hey, like I said. In my town, the shops are way smaller. (There is so much stuff here. I thought I was an experienced girl but handcuffs, bunny ears, dildos, vibrators?)

Jen took the blue dildo, and she was trying to feel it.

Jen: Hey, Elena, check this out!

Elena: Do you like it?

Jen: It’s too big for me, Elena!

Elena: That’s all right! I’ll buy it for me then!

Jen: I’d like something smaller.

There was a pink dildo, which was like 6 inches in size and was kept in the showcase.

Elena: What about this one?

Jen: Aww, that looks cute. I think it’s perfect for me! I want it!

Elena: I agree. It’s in your size! You should totally buy it!

Jen: Okay.

Elena: Congrats! You got your own dildo now! Nice!

Jen: Do you really have to tell that so the entire store can hear?

Elena: Yes, I always tell when I’m excited! C’mon, let’s go.

Jen: Go where?

Elena: To the hotel! We have to try out our new toys, of course!

The girls headed to Elena’s hotel room. They reached in half an hour.

Elena: Right, so How do you want to do it?

Jen: Do what?

Elena: Masturbate, silly.

Jen: I’m sorry, Elena, but how should I masturbate?

Elena: Well, do you want to do it by yourself? Should I just watch, or would you like some tips?

Jen: Well, I do like our experiments. Maybe you should help and give me some pointers.

Elena: Mistress Elena will aid you!

Jen: Okay, so Where do we start?

Elena: First, we get in the mood.

Elena leaned forward and kissed Jen’s lips. Jen obliged by kissing her back.

Jen: Then, we remove some clothes

Jen pulled her pants down.

Elena: Wow, someone’s an eager student.

Jen: Learning new stuff is fun, and like I said before, it’s fun doing this with you.

Elena: I like doing these things too. Now, let’s go to bed.

Jen: Yes, Miss Elena.

Elena pulled her pants down. Both the girls were naked from the bottom. The girls jumped and sat on the bed.

Elena: Now, then, if you want a dildo to slide into your pussy, we need to lube it up.

Jen: Elena, I didn’t get any lube from the store.

Elena: You didn’t?! Girl, trust me, the more lube, the better. Well then, if you don’t have any lube, we have to do it differently. Now suck it.

Jen: What?

Elena: Suck it, suck the dildo. Make it wet with your lips and your spit. Hehe, you could even practice some blowjob techniques.

Jen took her pink dildo and stared at it for some time. She then took the dildo head in her mouth.

Jen: Like this?

Elena: That’s good, but let’s practice like it’s a real dick. Guys love it when your tongue goes up and down their shaft. Keep your eyes open while you are doing it.

Jen was licking the dildo head with her tongue.

Elena: Wait, I have an idea. I’ll hold the dildo like a dick, and I’ll tell you how it looks.

Elena stood up and held the dildo near her pussy. She made Jen sit on her legs, and her face was just in front of the dildo. Elena kept the dildo on Jen’s lips.

Elena: What do you think of that?

Jen: I think it’s a bit weird, but I guess I never had an educational blowjob lesson before. So okay, I’ll give it a try.

Jen looked directly up in Elena’s eyes and open her mouth to take the dildo in.

Elena: Wow, I can see why guys like this.

Jen slowly took the dildo head in and started sucking it.

Jen: Do I look good? Am I doing it right?

Elena: You look beautiful, you little dildo cock sucker. Now honor your name and suck it. Try to take it deeper, guys love some deepthroating.

Jen: That’s when you nearly choke, right?

Elena: Kinda. Most of the time, I try to take a huge breath before I suck it in deep.

Jen: I’ll try.

Jen started sucking the dildo deeper. She could take it in half of the dildo.

Jen: Sorry, but I can’t go that deep.

Elena: Try again, and I’ll help you.

Elena kept her right on Jen’s head, and with her left hand, she pushed the dildo in and out of Jen’s mouth. She slowly pushed it deeper and deeper. Jen was able to take it almost all in. Elena pushed it deep and hard.

Jen: Hmmm! What the fuck, Elena! Fuck you! That’s not funny!

Elena: Hey, it’s what guys do all the time. You won’t say that to them as well, will you?

Jen: You’re not a guy. You’re my teacher.

Elena: I’m teaching you the art of giving head. But fine, I won’t do that again.

Jen: At least say if you are going to push me. Then I can prepare a bit better.

Elena: Okay, I’m sorry I will. Now lick the dildo. When you lick it, you should always look at your partner in the eyes. Now keep licking, but spread your legs and play with yourself.

Jen: Why?

Elena: Why, because it’s hot as hell! Besides for a guy, there’s no bigger compliment than you finding it hot as well to suck his dick. Now do it.

Jen followed Elena’s command. She moved her right hand towards her pussy.

Jen: Okay, Elena, I’m about to…

Elena: Stop!

Jen: What? Why?

Elena: Lay on the bed. I’m going to put it in.

Jen lay on the bed.

Jen: Be careful. A dildo is a bit different than your fingers.

Elena kept the dildo near Jen’s pussy.

Elena: Girl, trust me. You’ve lived up the dildo with your spit, and your pussy is already drenched. This is going to feel great.

Jen: You sure?

Elena: I’m sure.

Elena pushed the dildo head inside Jens pussy.

Elena: How does that feel?

Jen: That feels nice.

Elena: Yeah, you like being teased? Do you want it in you?

Jen: Yes, I want it in me.

Elena pushed the dildo in slowly. Jen’s body jerked a bit as half of the dildo was already in.

Elena: Wow, you nearly came already!

Jen: Almost, this feels great!

Elena: Well, then, wait till you feel this!

Elena started moving the dildo in and out of Jen’s pussy.

Jen: Please, faster.

Elena: Well, well, well. Someone wants to cum.

Jen: Yes, I want to cum. Please Faster.

Elena: As you wish. Faster it is.

Elena started fucking Jen faster with the dildo.

Jen: I’m cumming!

Jen experienced a huge orgasm. After a few minutes, she sat up.

Jen: That was amazing. I never thought it could feel that good.

Elena: Honestly, I was a bit surprised. My first time went really badly.

Jen: Really, I’m sorry to hear that.

Elena: Why don’t we use the blue dildo that I just bought?

Jen: What?! No way, Elena! It’s too big for me!

Elena: All right. Then why don’t you fuck me with it?

Jen: Are you sure?

Elena: Of course!

Elena lay on the bed.

Elena: This is going to feel great.

Jen: Do you want me to take off your top?

Elena: Nah, I’m fine. Just put it in!

Jen: As you wish…

Jen pushed the blue dildo head inside Elena’s pussy.

Jen: How does that feel?

Elena: Fantastic! You should try it out!

Jen: I’m not ready yet.

Elena: Keep fucking me, please!

Jen: Yes, teacher!

Jen started moving the dildo in and out. Elena’s pussy was stretching and closing due to the wave pattern of the dildo body. She was moaning like hell.

Elena: Faster…

Jen: Look now who wants to cum.

Elena: Yes, I want to cum. Please… Faster.

Jen: Your wish is my command.

She started moving the dildo faster. Elena was moaning heavily and was about to cum.

Elena: Cumming! That was amazing. I never thought it could feel that good.

Jen: Honestly, I was a bit surprised. I’ve never seen someone scream like you.

Elena: Promise me you’re going to try this dildo next time.

Jen: Elena, I told you, I…

Elena: All right, all right. At least try to masturbate with the pink dildo at home, okay?

Jen: Okay

Back at the airport, we landed successfully and reached home in a couple of hours. Amy called Elena to let her know that we were back. I took a quick shower.

Me: Honey, let’s go to sleep. I’m very tired.

Amy: Wait! Don’t go to sleep just yet, Dad. I have a surprise for you. Wait here. I’m just going to use the bathroom.

Amy came out after some time.

Amy: Ready daddy?
Me: Woah!

Wow! Amy was wearing the sexy transparent black lingerie, which we bought today. I must say that pantyhose looks pretty sexy on her. I could see her huge nipples through the mesh top.

Amy: You like?

She turned around and poked her butts out and was modeling me her entire body.

Amy: How does it look on me?

Damn, that ass looks amazing

Me: You look stunning, Amy. It suits you really well.

Amy: Thanks so much! The silk feels really good on my skin. Ready to go to bed?

Me: Sure, honey But first, can I take a picture of you? I love your outfit.

Amy: Of course, daddy! Whenever you’re ready!

I clicked a few pics and a few close-ups of her breast and that beautiful ass.

Amy: Do you mind giving me a quick massage before bed?

Me: Only if you give me a massage too!

She lay on her stomach. Her ass poking towards the ceiling. Wow! She sure has a fantastic figure. I started massaging her legs.

Amy: Mmm, that feels so good, daddy. You sure know how to make me feel great.

Then I slowly moved my hands towards her ass and started massaging her butt. I went behind her and started rubbing her shoulder.

Me: Honey, you are too tense. You need to relax.

I took her top off and freed her breasts.

Me: Feel ‘more free’ now?

Amy: I do, hahaha! It’s strange, isn’t it?

Me: I guess we spent too much time with Graham and Olivia.

Amy: We’ve picked up their nudist habits! Well, not entirely, I mean. Not me, I’m sorry you had to become completely naked when we met Koko.

Me: It is okay, sweetheart. It was a bit embarrassing for me at the beach. But I don’t care anymore. I did it for you, and I would do it again if I had to.

Amy: Thanks, Dad

After her shoulders, I moved to her boobs to massage them. Is she moaning?

Me: Honey, are you okay?

Amy: Yes. It felt really good, daddy. Sorry…

Me: Honey, I have already told you this, it’s not a big deal. Massages are supposed to be pleasant, and they can trigger all kinds of bodily responses. Nothing to be embarrassed about. Remember?

I could see she is a bit more relaxed now. I continued massaging her soft boobs. My, my, her nipples are so hard, and it seems she’s trying really hard to hold her moaning

Me: Amy, I can sense that you are still too stiff. This isn’t good for you. I don’t know if that’s the reason that you are holding back. Just so you know, I’ve heard plenty of moaning while massaging people. You should not restrain yourself.

Amy: Well, I just don’t feel comfortable about it.

Me: I’m your father, sweetheart. You don’t have to be ashamed when you’re with me. Anyway, it’s not like you can control the way your body reacts to any external stimulation. It’s nobody’s fault.

Amy: It isn’t?

Me: Well, no, not really. Sometimes you just react to sight or touch, or it can be something completely out of the blue. And guys have it even worse.

Amy: Really? How do you mean?

Me: Well, you know things might become hard to conceal when a guy is over-stimulated.

Amy: Oh yes, well, Koko told me the same thing today at the beach.

Me: She did?

Amy: Yes, when you came out of after the shower

Shit! Does that mean she noticed?! I presumed she hadn’t, but how could she not?

Amy: God, it’s so strange to have this conversation.

Me: Honey, I think I know what you are trying to say. Maybe you noticed me, I mean?

Amy: I did. At the beach, I saw you were a little aroused.

Damn it! This is so embarrassing!

Amy: And that wasn’t the first time I noticed your erection.

Me: What?!

Oh God! I screwed up!

Amy: I noticed it was like that at the bowling alley. I felt it in the hospital too.

Me: Sorry, dear. I don’t know what to say. I’m deeply sorry. Please forgive me.

Amy: Oh! No, dad, I didn’t want you to feel guilty. I’m telling you this now because actually, I’m feeling relieved. Maybe it was silly of me. But when I felt it, I really didn’t know what to think I was like, that’s really not something that’s supposed happen, is it? I was so confused.

Amy: So I just let it slide and pretended not to notice. But tonight you just told me that people can get over-stimulated because of random things, right? And that’s nothing to be ashamed of.

Me: Well yeah, that’s true. Sometimes an enticing view is all that it takes to get you a little worked up. Some other times it’s just a matter of skin contact. I guess that’s just how chemistry works.

Amy: Yeah, I thought it was something like that. That’s why I am telling you this now You told me that sometimes guys get really embarrassed because of this. And Koko said the same thing. Well, I don’t want you to be embarrassed around me!

Me: What do you mean, darling?

Amy: Well, you know. Since earlier, you were so patient with me without making it weird, I thought it was only fair to tell you that if sometimes you think I might notice your erections. Well, don’t worry about that. No offense was taken.

Me: Well, honey, I really don’t know what to say. I wasn’t expecting that…

Amy: Hah! So I managed to get you embarrassed for a change! Come on, lie down. It’s time for us to give you a massage!

What is she talking about? There’s no one else here.

Me: Where are you going, honey?

Amy: Wait here… You’ll see.

Amy went out of the room. What is she planning? No way! Did she invite Elena here? Damn it! No! It can’t be. She’s topless. Oh my! She’s holding the big teddy bear which she won during the cupid night.

Amy: Hahaha! This is little Aafi. And he will help me with your massage!

Me: Hahaha! You’re full of surprises, honey! Is he going to sleep with us?

Amy: I don’t know. Maybe he’s your son, you know?

Me: Pardon?

Amy: And I’m the mommy!

Okay, I think she’s really drunk I guess the champagne they gave us on the plane us still in her system

Me: Honey, are you okay?

Amy: We’re roleplaying, dad! I like roleplaying! Even if all my classmates say, that’s children’s stuff.

Me: Huh? Well, that’s not true at all! A lot of adults enjoy roleplaying.

Amy: I know, right?

Me: You bet! One time I even accompanied a friend of mine to this convention he always attended. It was full of adults roleplaying and co-playing – that’s the word, right? Well, they seemed to have a lot of fun, nothing wrong with that, right?

Amy: Exactly! You know, dad, sometimes I feel like you’re the only one who truly understands me.

Me: Hehe That’s because I’m your father, darling. We may have been apart for such a long time. But I always felt like I had a strong connection with you all this time. I just feel lucky that I got to spend some time with you again this week.

Amy: Me too, and I’m a lucky daughter. Now, on with your massage!

I lay flat on my back. Amy was sitting near my legs. She started massaging my legs. Oh my God! She’s so close to my crotch. Shit! I got a huge hard-on with Amy touches.

Wow! She is really ok with this. She’s really good! This massage is actually turning me on. Suddenly, Amy touched my nipple with her fingertip.

Amy: Your nipples are hard too! Hahaha.

She continued to massage my whole body. It was great. She was tired after giving me that massage. She’s lying on the bed on her back. I was sitting right next to her.

Me: Thanks so much for the lovely massage honey
Amy: You’re welcome. How about a good night kiss?

God, She’s just too sweet. So much so, it makes me feel a bit mischievous I’ll try teasing her a little.  I gave her a peck on her lips.

Me: But why just one? I think after that great massage, you deserve at least two!

I gave her another peck. This time I french kissed her.

Amy: Hahaha! Thanks, Daddy!

Me: And why limit ourselves to just one spot? There are so many places worth kissing you!

I kissed her nose. I then kissed her forehead. I slowly moved towards her neck and kissed her neck.

Amy: Oh, God, Dad, that tickles! Hahahaha! Oh, God, Daddy, stop! Hahaha! Please, you’ll make me, oh God, stop! Hahaha!

Me: Umm, Ok, you are excused. But as a penalty for trying to resist, another kiss on the neck!

I kissed her neck again.

Me: Okay, you behaved a little better this time. And now, let’s move south.

I moved towards her belly and kissed her belly button.

Amy: Wow! Oh God, I’m losing my breath Too much laughing

It’d be so tempting to go even lower to kiss her hips, to kiss her inner thighs, to kiss her… Nope, I’m not going to ruin the moment – time to move back up now.

Me: And it’s not over yet! North again!

I moved up and kissed her cleavage in between her breasts. My baby is having so much fun. That’s good. I wonder if it would be too much if I kissed those breasts too? Well, she’s ok when I look at them, she is ok when I touch them. Maybe she won’t mind if I…

Me: Last one!

I kissed her left nipple.

Me: Ok, you’ve paid your fee, you are free again. Hehehe

Amy was a bit dumbstruck.

Me: What’s up, honey?

Amy: Nothing. It’s just that You never kissed me there before and I don’t know

Damn, she is still so insecure. Maybe I went a bit too far. I’d better play it cool.

Me: Sorry, honey, I understand. Yeah, I guess I got a bit carried away. But you know how it is with me. I just like to cuddle you, and caress you, and kiss you.

Amy was pretty silent.

Me: The fact is you’re my baby girl. I simply cannot help loving everything about you. Your nose, your mouth, and your belly And yes, even your breasts, sweetheart. They are all the same in my eyes, all holy and special Because they all belong to you.

She was listening to me carefully.

Me: But if you didn’t like it, then I promise I won’t do that again.

Amy: (Dad seems so sincere. Maybe I’m overreacting again It wasn’t that bad) Huh? Oh, no It’s not that (Actually, maybe I liked it too much When he kissed me, I felt that Tingle down there again But how could I ever tell him that? God, this is so embarrassing) Sorry Dad, don’t mind me I know you love me and Yeah, that’s all right if you want to I was just silly.

Right, this is getting a bit awkward again. I need to lighten the mood.

Me: Well, If that’s the case, I’ll help myself then!

I kissed her nipple again.

Amy: Daddy! Hahaha, not again! That’s not fair!

Nothing is fair in love and war, dear! I kissed her one more time on her hard nipple. I started licking her nipple with my tongue. Moving my tongue up and down on her nipple.

Amy: Oh, God! Stop stop, please, stop, please! You’ve won, please!

Me: Okay, okay, I’ll stop. I’m getting tired. It was fun, though, right?

Amy: Oh, my ‘Fun’ you say? You almost killed me from laughter! You meany, Daddy! Darn you. But yes, it was fun.

Me: Hehe, I love you, darling.

Amy: Love you too.

Me: So, time for bed, then?

Amy: Yep, sounds good.

Me: Honey, I can’t believe all that happened today. I wish you could stay here with me forever.

Amy: Maybe I can.

Me: What?

Amy: Maybe I can tell mom that I’ll be staying here. I could go to school here. We could live together. Dad, I’m an adult!

Me: Okay, but how do we do that? We’ll have to come up with a plan.

Amy: Don’t worry. Starting tomorrow, we’ll begin with my master plan! You’ll see.

I was happy to hear that. We cuddled and went to sleep. Amy hugged her sex toy, the teddy bear.

Let me stop here, I will continue in the next part. More parts to come. Keep looking for this space to know what happens next. Please send me your feedback through email or hangout at [email protected].