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My Ex's Sister

"Babysitting my ex's sister get's more exciting than expected"

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Last week I went over to my ex-girlfriend’s house. I’ve always had a great relationship with my ex’s family and with her as well. The break-up between Kaitlynn and I was the best decision for the both of us, so we stayed friends afterwards. Her parents and little sister, Emma, also recognized this. From the time I started dating Kaitlynn till now, they’ve always been great to me. We mostly stay in contact with simple WhatsApp messages, but we also call each other from time to time.

A week before, their parents had asked me if I could babysit Emma while they were gone. Kaitlynn had some kind of festival that weekend and her parents were away on a business trip. Emma doesn’t need a babysitter, she’s sixteen years old. Her parents trusted her, so they knew she wouldn’t organize some kind of party while they would be gone. Emma just didn’t like to be alone.

Emma and Kaitlynn had a lot of things in common: they were fun to be with, they liked to be around friends and family and they were beautiful. Kaitlynn and Emma had similar faces and brown hair. The only difference is that Kaitlynn is nineteen and Emma is sixteen. Kaitlynn’s body is mature. She’s got some amazing tits, a nice figure and a nice, round ass. Emma’s body is still growing. She’s got small tits, a really slim figure and a small ass.

When I arrived, the family was still inside. Their father opened the door for me.

“How are you doing?” he asked.

“I’m fine, thanks. How about you?”

“We’re doing fine, but my wife and I gotta go now!”

His wife, also a beautiful woman, greeted me and walked with him towards the car. I was then greeted by the two beautiful brunettes.

“Hi,” Emma greeted cheerfully.

“Hey Dave,” Kaitlynn said.

“Hello ladies.”

We went over to the living room. Kaitlynn was packing the last things she needed for the festival.

“Dave, thank you for taking care of Emma,” she told me. “She really doesn’t like being alone, especially in the evenings.”

“No problem,” I answered.

We heard a car honking, so Kaitlynn looked outside.

“My ride arrived. Be nice, you two!” she said.

“Have fun!”

Emma and I watched some TV. Around 6 p.m., I decided it was time to cook some dinner.

“I’m going to make us some dinner, what do you want?”

“I don’t care, Everything you make is delicious,” she said.

I had cooked for them a couple of times before, every time with great success.

“I’ll go get two pizzas from the freezer,” I joked

Emma poked me between my ribs.

“Hey!”

“You’re a great cook. Can’t you cook something more special?” she asked.

“Sure I can,” I laughed. “I’ll go check what’s in the fridge.”

Emma was beaming with joy.

“I made sure we have everything for you to make lasagna,” she said enthusiastically.

“You’ll never get enough of lasagna, will you?” I said as I got up from the couch.

I walked to the kitchen and found the stuff I needed in the centre of the counter. I hadn’t noticed that Emma had followed me.

“That’s everything you need, right?” she asked.

I could see on her face she was a little nervous. I didn’t need to ask why. She didn’t want to disappoint me. Emma had always looked up to her sister, so when Kaitlynn and I started dating, Emma started to look up to me as well.

“Yes, it is,” I said.

“Good,” she said, clearly relieved.

Like I said, her family and I got along very well. But Emma was special. She really trusted me. She loved to be with her family. Every time we would watch TV, and Emma would sit on someone’s lap. It might seem childish for a sixteen-year-old, but that was her way of showing love and trust.

“Would you like to help me?” I asked Emma.

“Sure!” she replied enthusiastically. “But won’t I ruin it?”

“Of course not, sweetie,” I reassured her.

She sparkled when she heard me say the word ‘sweetie’. It was normal for me to call her words like that. I always did that, her family was okay with that. I didn’t mean anything by it, I just knew she liked it. The word ‘sweetheart’ does describe her quite well. She’s always been nice to everyone around.

“What do I need to do?” she asked.

I explained to her how she could help. We started to cook the lasagna and put it in the oven. The lasagna needed to be in the oven for about forty minutes, so we got on the couch and started to watch TV. Emma snuggled up to me and I put my arm around her.

When the lasagna was finished, we got it out of the oven. Emma was again beaming with joy.

“I’ll get the plates!” she said.

We set the table and sat down.

“Hmmmm... so good,” Emma said after taking her first bite.

I just smiled at her. It was nice to see her having fun. Emma had had a rough time. When Kaitlynn and I started dating, Emma was in a relationship with some guy. She was fifteen, he was sixteen. Their relationship didn’t work well. That guy was really bossy, always telling Emma what to do. When Kaitlynn celebrated her nineteenth birthday, things got out of hand. Emma refused to do something for him and he hit her. Obviously that was the end of their relationship. Emma had had more bad relationships. Kaitlynn had as well, but when Kaitlynn and I were together, we were always smiling and having fun. Emma got jealous, I guess. I thought it was normal, everyone wants a good relationship. I’ve seen her at her worst, right there at that party. Now she’s having fun again.

We finished eating and watched some more TV. Again Emma snuggled up against me.

“I like you,” she mumbled.

“What did you say?” I asked, thinking I misheard her.

“I like you,” she said, looking at me nervously.

“I like you, too,” I said, but I didn’t mean anything by it.

I just liked her, as a friend. Emma smiled when she heard me say that I liked her, but she didn’t look satisfied.

“What’s wrong?” I asked.

“I want you,” she said.

I was shocked.

“What do you mean?”

“I’ve seen you with Kaitlynn. You’ve always been nice to her, even when she wasn’t,” she said.

“We can’t be together, you know that,” I said as I started to get worried.

“Just once, please?” she begged.

“Emma, sweetie, you can’t be together for just one time. A relationship is serious, it’s for a long period of time,” I tried to explain, struggling to find the right words.

Emma wasn’t stupid. She knew we couldn’t be together.

“I don’t mean that I want a relationship with you,” she started. “Well, I want it, but I know we can’t. I just want to spend one night with you.”

“Emma, no, come on,” I said.

“Just once, nobody will find out,” she said, trying to convince me.

“We can’t have sex, you’re too young,” I said.

“Please, Dave. All my friends are getting deflowered, yet here I am. Still a virgin. They’re all laughing at me,” she said, tears forming in her eyes.

“They shouldn’t do that, Emma. They aren’t very good friends if they do that, are they?”

“I know, but I just want to know what it’s like,” she told me.

“There’s nothing wrong with being a virgin. Kaitlynn was my first, so I was nineteen when I first had sex. You’re just waiting for the right guy,” I said.

“You are the right one, Dave,” she said.

My cock was starting to get hard. I loved her, in a friendly way. I couldn’t make her sad. Also she was pretty. Her beautiful young, yet mature, body was turning me on. Her small tits were hugged by her tight, white shirt. I hadn’t had sex in a long time. I knew I shouldn’t have done it, but I couldn’t help myself. Emma had successfully seduced me.

While my right hand was still holding her, I moved my other hand towards her. I let it rest on her stomach, before slowly moving up towards her small tits.

“You want to feel what it’s like to be with a man?” I asked.

“Yes,” she said.

“Just for once, okay? After it’s done, we will never talk about it, understood?”

“Yes.”

I started to caress her tits. She moaned softly. Emma had a scared look on her face, after all it was going to be her first time.

“If you want me to stop, just say so,” I said.

“Please continue,” she said, as she placed one of her hands on the now clearly visible bulge in my pants.

We were still on the couch in the living room. If Kaitlynn or her parents would enter the room, we would be caught. We needed to be safe.

“Let’s go to your room,” I suggested.

“Okay,” she said.

We quickly went upstairs and entered her room. Emma walked over to her drawer and grabbed something. As she turned around, I saw she was holding a condom.

“I saw some of those in Kaitlynn’s room, so I grabbed one when she was gone yesterday,” she explained.

“So you planned this?” I asked.

“Yes,” she smiled.

I walked over to her and placed my hands around her thighs. I leaned in for a kiss, which Emma returned. I slowly pulled her shirt up. Emma was still nervous, so I made sure to go slow.

As the bottom of her shirt almost reached her tits, I stopped.

“Are you ready?” I asked.

Emma just looked at me and nodded. I pulled her shirt off. I stared at her small tits, which were still concealed by her red bra.

“I know they’re not as big as Kaitlynn’s, but are they nice?” Emma asked me.

“Yes, they are. Don’t worry, Emma, your body is amazing,” I soothed her.

Emma and I stood still for a moment, both unsure about what to do next. I decided to pull off my shirt. After I did, Emma still didn’t know what to do. I walked over to her. Emma just watched me, not moving a muscle.

“Emma?”

“Yes?” she said, still not moving.

“If you don’t want this, we’ll just go back downstairs and watch some more TV.”

“No, please. I want this. I just don’t know what to do,” she explained.

“Let’s both take of our pants, shall we?” I suggested.

Emma placed her hands on the waistband of her pants and waited for me to do the same. I first had to unzip my trousers.

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Then we both pulled our pants down. Now both standing in underwear only, we stared at each other’s bodies.

“Do you like my body?” Emma asked.

“Yes, I do. Do you like mine?”

Emma nodded. I walked over to her.

“Is it okay if I unclasp your bra? I would love to see your breasts.”

Emma moved her arms up, so I could unclasp her bra and get it off of her. As I did so, I finally got a look at her tits. I moved both my hands to her tits and softly squeezed them.

“Hmmmm.”

I moved my hands down towards her panties. I looked into her eyes. She smiled back, I took that as the ‘okay’ sign.

I pulled her panties down. To my surprise, her pussy was shaven. I moved to my knees and started to kiss her stomach. I slowly moved down towards her pussy.

“Do you like it?” she asked.

“Yes, I like it very much,” I answered.

I started to lick her pussy. Emma squealed.

“Can I lay down on my bed?” she asked.

“Of course,” I replied.

She walk over to her bed and lay down. I moved to the bed as well and put my head back between her legs. I resumed licking her pussy. I wanted to make sure her body was ready. I put one finger inside her, while still licking her clit.

“That’s sooo goood,” Emma moaned.

I continued doing what I was doing, my cock almost bursting through my boxers.

“I’ve waited for this moment for so long, “ Emma panted.

Her fantasy was now real. The way I touched her pussy, which was perfected when Kaitlynn and I were together, became too much for her.

“Oh, oh, ooohhhh,” she moaned.

She put her hands on my head, making sure I wouldn’t stop. Her body was shaking. After a while, Emma came down from her orgasm.

“That was great,” she said.

She looked at me with a shy smile. I moved up, holding my head over her tits. I sucked on both her tits shortly.

“Should I please you now?” Emma asked.

“I would like that very much, but you don’t have to do that if you don’t want to,” I said.

“I wanna try,” she said enthusiastically.

I got off the bed and stood next to it. Emma moved over and lay on her stomach, her head just inches from my contained cock. She looked up at me and I nodded. She placed her hands inside the waistband and pulled my boxers down. My cock was finally released and bounced up and down. Emma’s mouth was wide open.

“It’s bigger than some of Kaitlynn’s toys,” she said.

“Have you used them?” I asked.

“No, I didn’t want to. I only used my fingers,” Emma said, her face flushing red in embarrassment.

“There’s no need to be embarrassed,” I told her.

Emma was unsure what to do with my cock. She kept looking at it. She grabbed it with her hand and started to move up and down slowly.

“Emma, it might be easier if you sit on your knees,” I suggested.

Emma got up. I grabbed a pillow from her bed, so she wouldn’t have to sit on the ground. I was a little surprised when I found a small dildo lying under her pillow.

“I thought you said you didn’t use toys?”

“Okay, I did… but only this one, Kaitlynn bought it for me when she caught me in her room, looking at her toys,” Emma explained.

Her face was red before, but nowhere near as red as it was now. She just looked down to the ground.

“It’s okay, don’t worry,” I said as I dropped the pillow on the floor.

Emma got on her knees. I took the dildo from her bed and gave it to Emma.

“You can play with it, if you want,” I said.

Emma smiled and moved the plastic cock to her pussy. With her other hand she started to stroke my cock.

“Sweetheart, that’s great,” I encouraged her.

Emma was smiling again. She moved her mouth closer to my cock. She opened her mouth, but then hesitated and closed it again.

“You don’t have to suck on it,” I said.

Emma seemed determined to go all the way, as she opened her mouth again and licked my cock. She licked my member a couple times more, before slowly sliding it in her mouth. She closed her lips tightly around my cock.

She was still very aroused. She was using her dildo and it was having an effect on her. Emma moaned on my cock, which felt great for me. She started to bob her head up and down. After a while of sucking, she stopped.

“Can we… you know?”

“You want me to fuck you?” I asked.

She nodded.

“Are you sure?”

“Yes,” Emma answered.

“Okay. Can you lay down on your bed like you did before? I’ll get the condom and put it on.”

Emma did as I asked. She dropped the dildo on the floor and walked over to the bed. She lay down and spread her legs. I had grabbed the condom and climbed onto the bed.

“Could you help me?” I asked her.

“Sure, what should I do?” she asked.

I placed the condom at the head of my cock.

“Could you put the condom on for me?”

“With my hand or my mouth?”

“Your mouth would be great, but your hand is fine,” I said.

Emma motioned for me to get closer to her head. I moved so my cock was close to her mouth. She held the condom in position with her hand, before moving her mouth over the condom and my cock, making sure my cock went inside the condom. She rolled the condom out over my cock and kept sucking me off for a couple of minutes.

When she stopped, I moved down.

“Are you sure?” I asked again.

“Yes,” she answered.

“Do you think you’re wet enough? Do I need to lick you some more?”

“Please just put it in,” she begged.

I obliged. I positioned my cock against her wet opening. I slowly moved my cock forward, the head of my cock was quickly engulfed by her pussy.

“Ooohhhh,” she moaned.

“Can I go further?”

“Yes, please.”

I moved forward slowly. Her pussy was incredibly tight. Kaitlynn was tight as well, but that was nothing compared to her virgin sister.

I decided it’s sometimes best to take one step back, to go two forward. I pulled my cock out for an inch or so.

“No, don’t pull out!” Emma said.

“I won’t, trust me,” I said.

Emma looked at me and decided she would let me handle it. I pushed in again and my cock went further into her pussy.

“It hurts a bit,” Emma said.

“That’s normal, honey. It will get better,” I said.

I pulled back again, before slowly thrusting inside. I kept doing so for a couple of minutes to let Emma get used to the feeling of my cock inside her pussy. Emma started to moan louder.

“It feels so good, please go faster,” she moaned.

I leaned down. I could now feel her small tits against my chest. She put her arms around me, holding onto me tightly.

I picked up my pace. I knew I wouldn’t last long. Her tight pussy felt like it wanted to milk my cock, making sure no drop of cum would stay inside my body.

“Sweetie, I’m close,” I warned her.

Emma didn’t pay attention to my words. She was moaning loudly.

I pulled away from her. She realised what I was doing and let her arms drop to her sides. She moved one hand downwards and started to play with her clit. I could tell she was close. I moved my head and started to suck on her tits. I kept fucking her at the same speed. Her moaning got even louder.

“I’m cumming!” she yelled.

Her body started to shake and her pussy muscles contracted around my cock. The sensations of her pussy walls tightening around my cock were too much.

“Me too,” I groaned.

With Emma still shaking, I started to empty my load in the condom, my cock still buried inside her pussy. We moaned together, our bodies drenched in sweat.

When I calmed down from my orgasm, I realised what I’d just done. I had fucked my ex’s sixteen year old sister. I felt ashamed for fucking the young woman, I should have resisted her advances. I looked down, seeing my cock still in her pussy. I slowly looked up. I saw her small body, her tits, and finally her face.

“That was great,” she said. “How was I?”

“You were great, sweetheart,” I told her.

“Are you okay?” she asked.

“I’m fine, how about you?”

“I’ve never been better. I finally know what sex feels like. I wish we could fuck for the rest of my life.”

I smiled. I still felt bad for what I had done.

“Dave, I wanted this, I really did. I have no regrets. I hope you don’t have any,” she said.

I pulled my cock out of her wet pussy.

“Let’s get dressed,” I said.

Emma and I got up from the bed. She tossed a towel at me.

“That’ll help,” she said with a smile.

We dried ourselves and got dressed. When I was done, Emma walked up to me and hugged me.

“Thank you, Dave,” she said.

I kissed her on her head as I held her close. We went downstairs and watched TV again. Emma sat on my lap and curled herself into a ball. I kept my arms around her and caressed her body.

“I love you,” she said.

Emma was tired, so she soon fell asleep. After an hour, she woke up to the sound of people talking and a car driving away. Kaitlynn was home.

“Hey guys!” she said as she came in.

“Hi,” I replied.

Emma didn’t say anything.

“She was sleeping, wasn’t she?” Kaitlynn asked.

“Yes.”

Kaitlynn walked over to Emma and kissed her on her head.

“Sorry I woke you up,” she told Emma.

“I’m going to carry her to her bed, I’ll be back in a minute,” I told Kaitlynn.

I walked up the stairs with Emma in my hands. I put her down on her bed. There was a clear wet spot on the bed and the room smelled of sweat and sex. I opened a window so the others wouldn’t be able to smell it. Emma was asleep again. I closed the door and went downstairs.

“She didn’t cause any trouble, did she?” Kaitlynn asked, before yawning.

“No, she was great,” I said.

“Good,” Kaitlynn said. “Well, I’m home now, so you can go if you want. I’d like to talk to you, but I’m so tired, it’s better if I go to bed.”

“I’ll go then,” I replied.

I walked over to Kaitlynn and kissed her on her forehead. We looked into each other’s eyes and both smiled.

“Bye,” she said as we walked to the front door.

“Bye,” I answered as I walked outside.

I walked to my car and thought about what happened. I didn’t feel bad anymore. I was satisfied, Emma was happy, so why would I feel bad?

“Dave!” Kaitlynn yelled from the doorway.

I turned around.

“Thanks for staying with my sister. She really enjoys spending time with you,” she said.

“No problem.”

“Goodnight,” Kaitlynn said.

“Goodnight,” I answered.

Kaitlynn closed the door and I got into my car. I drove home and got into my bed. I never expected things to turn out the way they did. I just hoped nobody would find out what happened between Emma and I.

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Written by ilp99
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