Lily’s Advance

A man meets a girl on a walk at night and she takes a liking to him.

First of all, this is a totally fictional story and is meant for fantasy and nothing more. Everyone in this is fictional and not based on a real person.

My name is Connor and I am in my mid thirties living by myself. It’s a quiet life, I have my cats and that’s it. So often in the summer once it starts to cool down I’ll go for long walks around my city. I might go until late at night sometimes, hours and hours. I live in a safe city, so I never have anything to fear.

Usually I’ll take a short walk around 4 or 5 through the park for maybe an hour. Later, at around 9:30, I’ll head out for a multi hour walk. That’s where I met Lily.

One night I had decided to walk the track on the local high school, it was a perfect June night. As I was walking and lost in thought a girl came behind me on a long board followed by a boy. They startled me but I laughed and waved, she said sorry.

I decided to do one more lap, and they came up a few times more, it was dark so I couldn’t see them that well. I saw that they were leaving and thought I’d do a half one and exit the back property of the school when a girl called out and startled me. “Hey!”

“Hey, oh god sorry you startled me again.” I said laughing at how skittish I was. “I thought you both left?” I asked as I walked over to see her leaning against the equipment shed under the only light.

There she sat under the light. Legs out, one bent, in ripped jeans short-shorts. She had a sparkly blonde ponytail, big cheeks, braces, blue eyes, a little acne. She had an adorable giant smile and was cute! Her legs were long and skinny and her sweatshirt was cut to see her flat stomach and small to medium boobs it seemed. “He wanted to go home, I told him I wanted to stay out longer. Come sit with me!” she insisted.

I looked at her quizzically “What’s your name and uh… how old are you?”.

She rolled her eyes and then smirked at me “I’m Lily, 14, but no one can arrest you for having a sit. How about you?”. She had so much confidence it was sexy, god I shouldn’t think that!

I smiled and shrugged, she wasn’t wrong. Whatever, I could use a rest anyways. “Fair enough, and Connor, 34.” I said and put out my hands. “If that’s too old I get it, it’s weird, I can go.” I pleaded. I just didn’t want to be a pedo, god what if someone saw!

Lily playfully grabbed my arm and pulled me down next to her. I could’ve fought but I laughed and so did she and I relented sitting about six inches from her against the shed. I won’t lie, it felt good when she did that, just touching me. What was I thinking, she’s 14! “Here, Connor, have some water.” she teased and pushed her water bottle into my face.

I was very thirsty and not near a water fountain so I took a drink. I’ll never forget that the rim was warm and tasted of cherries, her lipgloss I’m sure. Lily laughed and told me that I drank loudly. I laughed back and said I know and don’t really care. We kind of laughed and joked around for maybe 15 minutes.

She told me a bit about her family life and how she never had a dad or stepdad, he died when she was young I guessed or disappeared, wasn’t going to pry. She also said she lived around here and that she just needed to be home in an hour or so she told me, her mom wasn’t very strict.

I took out my THC Vape and she took out her own and we laughed. I was kind of relieved because that meant she wasn’t going to ask for mine, I wasn’t giving drugs to a minor. I looked up and realized we are basically under a spotlight to everyone nearby (it was in the center of a neighborhood). “Hey we should probably move, lotta cops come by and you’re a minor.” I scratch my head “I should probably go home.”

She kind of looked at me oddly for a second and jumped up next to me and stretched “Yeah you’re right, same.”. Just as she said this she brought one arm down around my midsection and another carrying her longboard. “I’m sorry but could you walk me home, I don’t live far at all, maybe 15 mins away? Please Connor, it’s late!” Lily asked and then pointed behind me.

I turned around with Lily still under my arm. She was maybe 5’1 (155cm (shout out to all of my non-American friends and readers)) and had a skinny body with a toned but small butt. It was still pronounced though, as were her maybe b cups. I asked myself “What was wrong with me?” a thousand times and each time ignored it and played it off.

But standing next to me? She looked like a little girl at my 6ft (183cm) and slightly out of shape frame. She was going my way anyways and could you imagine how bad I would feel if something happened to her? “Yes of course, I should’ve offered anyways. Where do you live now?”

“I’ll tell you as we go.” she said and walked hugging me almost. I sort of resisted a bit before she interjected “Sorry I’m cold, this doesn’t cover much and you’ve got a hoodie at least.” She looked up at me with those doe eyes.

“Oh of course it’s fine, and let me carry that for you also.” I insisted on, gesturing to her longboard. It was then that her mom texted. I guess Lily’s mom is working an all night shift and won’t be back until late in the morning. I gulp knowing what this means.

We actually saw her mom from far down the street, she knew the taillights. I was a bit relieved she didn’t see a grown man dropping off her daughter. The whole time Lily kept rubbing me more and more, her hands traveling to my chest and stomach. I tried to ignore it as best I could. “This is it!” she piped up.

The house was older, kind of run down but not too bad. As we approached her steps I felt the urgent need to be pee “Do you mind if I take a quick piss inside?”

Lily smiled and invited me right inside. As I went into the house I noticed it was totally quiet and a bit messy. Lily told me it was the door at the end of the hall, I walked down peering into her room as I passed it. A small room with clothes all over the floor, a pink and white bed spread with white walls. As I left the bathroom Lily pulled my arm into her room and started kissing me. “Lily, what are you..” I protested but she just pushes me back into he bed as ashe kissed me.

“Quiet now.” she whispered into my ear as she straddled me. I was so turned on, I could feel her legs on either side of me and my lips started to betray me and kiss her back.

“Lily, please… this is wrong. I could go to jail.” I tried to argue but she wasn’t having any of it. She grabbed my hand and put it right on her ass, which was bare I now realized. I couldn’t help but squeeze and feel her tight teen ass. It felt so good but I caught myself and started to try and get up.

Lily pushed back and wrapped herself around me. I struggled a bit and then she went to my ear “You know you want it, besides at this point why not? You’re already in the room with me with my pussy out, you’d be in trouble anyways.” she declared. She makes great points, I feel for her future husband!

Truth is, I didn’t need much convincing, I wanted this. I could deny it to myself all I wanted but I wanted her so bad. Her being 14 was scary, but the rush made it all the more exciting. To have this sexy teenager all over me was more than a dream.

It was then that I decided I’m going all in, and I flipped her over and began to kiss her from above. She squealed in delight as my lips began to attack her chest. I threw off her shirt to reveal her perky little teen tits, they were about a B and so gorgeous. I took her entire left tit in my mouth and sucked hard onto it.

Lily was moaning and putting her hands through my hair, begging me for more and more. My hands behind to search to play with her little clit, it was as if my fingers were drawn to it. My kisses strayed from her boobs to her tiny little slit.

She was hairless, waxed I think, and it was leaking a bit of glistening juice. The outer lips were large and puffy and hid her little treasures. I kissed her thighs and bit them a little and heard her make a gasp. Finally my tongue danced to the sides of her fat pussy and licked them, teasing her.

It was with great relief to her that my tongue finally graced her clitoris. I began to lick at it hungrily. She twitched a little, jumping at the zap of pleasure. I kept kissing and kissing and snaked my tongue up her slick tunnel.

She was pouring out her little liquid and I could’ve drank it for hours! She tasted like heaven, I felt like a hummingbird who just found the most succulent of flowers. My tongue invaded her and scooped and sucked trying to get all the juices into me.

I went back up and began to lick her clit more and more while my fingers worked her hole. Within a few minutes Lily was having a powerful orgasm. She tensed up and then began to heave and thrust into my face. Her breathing became deep and she moaned loudly, her hands twisting the sheets. All the while my tongue never stopped working.

“I need you, please fuck me, I need your cock.” she begged as her orgasm began to make her tremble. I began to work my lips up and kissed her little mouth that now was huffing and puffing as it all passed her. I brought my cock to her entrance and rubbed the head onto her clit. She moaned more and jumped.

Slowly I lined it up and began to sink into her tiny pussy. It was so tight, she was so incredibly tight. Her hymen was broken so I didn’t have to worry about that at least. She winced and moaned as my cock went deeper and deeper. I was moving so slowly it felt like I would never reach the end until finally my crotch rested against her pubic mound.

She smiled and looked up at me. “I’ve never had a real cock before, just a hairbrush.” she admitted and blushed. I asked her if she was okay “I’m amazing! It feels so fucking good!” she cooed as she kissed me.

Slowly I began to pull back and then slide back in little by little. After a few minutes I worked up a rhythm and she began to rock towards me. We were in synch “You’re doing so well, you’ve got it down.” I praised.

Lily smiled like a little girl “Thank you so much, it’s easy with you Daddy.” she said. My cock spasmed at the word daddy, it was so sexy. I was fucking her good now and she was moaning.

I flipped her over and began to fuck her in doggy. Her ass stood begging for my cock and I was happy to oblige. I was fucking her hard now and the whole house was filled with the echos of me slapping against her ass. I was in heaven, this 14 year old had the best pussy I’d ever felt.

“Fuck me daddy! Fuck me daddy!” she kept shouting with each new thrust and it was too much. I couldn’t last any longer and I began to spray her tiny little pussy full of my hot cum. I buried myself to the hilt and painted the inside of her with the biggest load I’ve ever had.

“Oh my god yes daddy! Put a little baby in my teen pussy!” she cried out. I didn’t care in that moment, I was so happy. As I fell back onto the bed her pussy squeezed every drop from me like a finger pushing it out. She laid next to me kissed my cheek. “I love feeling you drip out of me.”

I laughed a bit and realized how crazy it was what I had done. We kissed and made out and I held her while she fell asleep before slipping out and going home. Overall my first time with Lily was probably the craziest thing that ever happened to me up until that point, she really was perfect.

Hey, first story, hope you like it! I’ll add my session, any girls can HMU if they liked this 🙂

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