Little Dilemma (Pixiv Fanbox)

LittleDilemma_AllVersions

No pixels & Alts here! ⬆️⬆️⬆️✅ (All versions shaven&pubies)

LittleDilemma_OnlyPubies

Only pubies versions here! ⬆️⬆️⬆️✅

LittleDilemma_OnlySoft

Only shaven versions here! ⬆️⬆️⬆️✅

Just a little girl and her mother. You're into a little dilemma. She hooked you up with her mother a few days ago but you have already know her or seen her at least in one of the student-parents meetings. She got tired of listening to her mother cry and masturbate to sleep since she hasn't had even a single date for years now. She knows you're not an asshole so she came up to you one day after class asking you if you could quote "help her mother get laid". That's not a request you get everyday from your students. You have seen her mother before in the parents meetings and school events. But going out with a mother of one of your students? That does't seem too appropriate. You refused of course. She turned around angrily and walked out the classroom. The next day she came to you with the same request. And the day after that, and the day after that. You even received a text with the same message. "Please go out with my mom." She kept insisting the next few days. It seems she got tired one day. When her mother came to pick her up you saw her just talking to her mom through the car window instead of entering the car. Her mom drove away and you saw her parking her car. This doesn't seems good. Her mother opened the door and got out of the car. You saw her crossing the street with her purse on her hands. She came up to her daughter and you saw her telling her mother something. She then pointed towards you. You made eye contact for a second with your student as she gave you an angry look but also with a faint smile knowing you had no escape. Of course you saw both of them walking towards your direction. Shit. Is she for real? You thought maybe she was joking all these days but she is actually walking right now bringing her mother alongside her. You thought of maybe escaping but you can't run. That would be weird and it's too late to go away walking since they are just meters away. You scratched your head and looked in every direction except theirs.

"That's him mom." You heard your little student say.

"Oh. Yes, Mr-" Her mother said before getting interrupted by her daughter. She had her hand extended towards you.

"Mom he wants to take you out on a date."

"Oh my! Emma!" She said to her daughter as she brought her hand to cover her mouth. She immediately looked at you. "Is this true?" She said with her hand still covering her mouth "She told me you had something to tell me but I thought it was school related or that maybe she got into trouble or something but you-"

"Mom quit the fuss!" She said before her mother could continue talking. "You can ask her now" she said to you. What? She is now demanding you to ask her out when you have repeatedly said no to her idea. You do admit that she is pretty. Maybe a little old for you, but you can tell she might be quite pretty when she was your age. She is what? Maybe 10-15 years older than you? Same age difference you have actually to little troublemaker Emma right here. You can't tell about her body. She seems like a proper lady. She has a long skirt and a very lady-like coat. Seems like she just returned from her work at an office. She is blonde like her daughter but she has her hair straight unlike her daughter who always has these twin pigtails. To be honest she does look kinda prett- "I accept!" You heard her mother say.

"What?" You asked confused.

"I accept your proposal to go out!" She said happily. Her evil daughter was standing there with an evil smile looking at you.

"Well I- Um. You see- um, I-" you kept stuttering

"Are you free for a cup of coffe this Thursday?" She asked you.

"I um- yeah. I-" you got quickly kicked at the shin.

"Yes, he already told me before you came he wanted a cup of coffee with you" Little Emma said to her mother. You were trying to dissipate the pain of your leg with your hand.

"Oh my! Splendid!" Her mother said. She went into her purse and took out a small notebook. She started writing something with a pen. You were looking angrily at Emma with your leg still being in pain because of her kick. Her mother ripped the little note from her notebook and handed it to you. It had a number followed by her name on the bottom.

"So you can call me when-" She was going to say before getting interrupted by her daughter.

"Yes okay fine lets go!" She started pushing her mother away placing her hands on her mother's back.

"Oh my!" You heard her mother said in the distance as they were both walking away.

"You're welcome!" Emma turned around to yell at you.

Her mother turned around and waved goodbye at you with one hand as she kept holding her purse with the other one. They both made their way towards her car.

You stayed standing there with the pain wearing off, holding a little note with your student's mother's phone number as you were set on a date with her already.

How did you ended up in this situation? You are asking yourself. You went on Thursday on a date with her. It was actually kind of nice. She seems really proper and relaxing. A coffee date seemed to match her pretty well. You both were on a date and she came in wearing her usual long skirt with a coat. This time she was also wearing a scarf. As a man of course you were also curious about her body. But she didn't let much room for your eyes to search for it. Regardless, her face was everything you had to see. Her personality did the rest. She is very soft spoken. You started wondering how her daughter turned out to be the complete opposite of her. You have actually sent Emma to detention a few times for inappropriate use of her uniform. Wearing a skirt that is clrearly meant for girls 5 years younger than her exposing her underwear, sitting with her legs wide open for everyone to see, purposefully not wearing anything below her clearly seethrough white shirt, and the list goes on. The total opposite of her mother as it appears. You both talked about life, your jobs, and of course she told you a little bit about how it is to raise a kid by her own. You made sure to leave Emmas misadventures out of the conversation.

Overal the date went really well. As you both walked outside the cafe towards her car she extended her arms and placed them on top of your shoulders as she leaned to kiss you. Her lips were soft. Her lips kissed and brushed yours a couple of times. As pulling away slowly it seemed she snapped back to reality. She looked at you widely and immediately brought her hands to cover her mouth in shock.

"Oh my! I'm so sorry! How improper of me! I got carried away, I'm sorry!" She said apologizing to you.

You both stared at each other and started to laugh. She was laughing a little more nervously as she was a little ashamed to kiss you out of the blue.

"That was my first kiss after 10 years" She said nervously with a smile with her hands on her cheeks trying to hide a little her face.

"That was my first kiss with one of the mother's of my students." you said.

She laughed as she understands you are both on a similar situation.

"Would you like to go on another date next week?" You asked her.

She smiled and nodded with her head. "Absolutely. Please call me." She said.

She hugged you and you both waved goodbye as she got into her car.

Well. It seems you indeed just kissed her mother and you are now dating her.

You felt a buzz on your pocket. You got a messge. You reached for your phone. It was a message from Emma.

"Last night mom masturbated moaning your name. That's some progress. How is your date with her?" you immediately ignored her message and placed your phone back to your pocket.

Now. The situation you were in, well, you are currently lying on the floor as you almost fainted. Youre lying on the sand to be more precise. It turns out little Emma here arranged a date on the beach. It was just like half an hour driving so you accepted. Your second date being on the beach? Well you dont have a clear excuse as to why not. The day is pretty nice actually so it seems it will be a good date.

You parked your car and made your way to the beach. Emma was instructing you as to where you will meet up with her mom. You stayed on the beach looking at your phone. There was a small problem. Emma started setting "conditions" to date her mom. What does she means? She was demanding you to go live at their house by the end of the month. She is obviously joking rigt now.

"She really likes you, so you can be my father now," she said in a text.

She is really taking things way too quickly isn't she? You kept ignoring her messages as usual. There were a bunch of messages with not a single response of yours.

"Also, you should have sex with me as well." Another text popped up.

What?! What is she talking about? She really must be joking right now,

"If you are going to date my mom, you have to date me too. You can have more sex with mom if you want, but you have to do me too."

Are you reading this correctly? Did you got a message of someone else by mistake? No. That is her name and that is her dumb face on the profile picture.

"We will have threesomes as well. I've already told mom that you both wont date anymore if we don't have at least one threesome per week. She agrees."

"Anyways are you there yet? We are on our way"

What is she talking about? She says she already told her own mom she wont allow HER to date you if she doens't has sex with you as well? Since when does she wants to have sex with you? You thought this whole thing was so you could date her mom, not her! But well it turns out you will date her mom AND her?!

You felt a little tap at your shoulder. As you turned around you got quite a view that your legs quickly stopped functioning properly. First of all, Emma was wearing the smallest bikini that clearly wasn't covering her properly. Her nipples were about to be visible if she moved her bikini just slightly and her clit was clearly visible. It seems on purpose it is leaving THAT spot visible to everyone. And second of all, you had absolutely no idea her mother was... well, how could you describe it? Her body was something you only saw on videos you shouldn't be watching at school hours. She was wearing sort of a matching bikini of Emma's. Her nipples on the other hand were bigger and thus her areolas were visible even with the bikini on. Her boobs and hips were just emanating an aura of fertility. Her body didn't matched at all her personality. Her privates were also exposed. She was standing there looking at you as you could see how she was ashamed of how she was presenting to you currently.

"Oh my. Emma this is so inappropriate, everyone can see our boides. Are you sure you don-"

"nonsense mom." Emma said. "Hey you." she directed to you as you were on the ground. "How do we look?"

"Emma..." Her mother said.

Emma kept looking at you waiting for an answer.

"Im so sorry. Emma made me wear this. She said... she said I could impress you this way."

Impressed you are. You are just out of words. Not just by the sight, but the whole situation. You are looking at two complete opposites. Both girls have feelings for you. One of them is your student, a little girl that is just hitting puberty. The other one is her mom, a woman past her prime but somehow it looks she might be even better than in her prime days. One of them is a pervert outgoing little girl, the other one is a proper soft spoken lady. And you are completely hating this moment right now. You never thought you would get attracted to a little girl like her. Her mother? Of course. She is an adult and the limited time you had with her was wonderful. But the little girl who is beside her is now popping up in your head with her bizarre confession to you. One is small and flat. The other one is big in all senses. Even if you are taller than her mother, her height might have gone to other areas as you can see. Do you have a choice? She already told you your choices. You have to date both of them. Your life just turned upside down thanks to Emma and her mother. You are now in a little dilemma.