Archive for the 'Underage Roleplay' Category

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Submissive Babysitter

It was his wife that approached me about the babysitting job. She felt that I was not a threat to her family like the last babysitter was. Sadly, she was wrong. I really liked her and never meant for this to happen. Her husband is always watching me I can feel his eyes shift around the room every time I move. After a week of watching this I decided to play his game. He was making me feel sexy. I started running my finger across my lips and putting them in my wet mouth. He would watch me with his mouth wide open. It was fun watching his cock bulge through his pants. After a long day with the kids, I was tired and ready to go home. That’s when he called me into his study. He had his pants pulled down stroking his cock. He told me I was a bad babysitter the way I have been teasing him. I backed up against the door with my hand on the door knob. I wasn’t sure what to think. He looked angry he shouted at me if I wanted to get paid for my dues then I better listen to him. I then moved closer to him and my eyes grew wide. He grabbed my hands and placed them on his cock and I proceeded to give him a hand job. I couldn’t take my eyes off of him. All of a sudden I found him to be attractive in a way that I never thought of. He lifted my skirt pushing his fingers into my tight little cunt making me cum all over his fingers. He told me he was going to turn me into his slut and to be prepared to serve him. I smiled and said thank you and took my babysitting money. This was nothing like my last babysitting job last summer. I’m ready to go back today just to see what happens.

Baby Girl Emma

I get so jealous

I have been staying with an “older” man since he lives in the school district of where I wanted to go. Who is he? He could be my step brother,  an uncle or maybe I will keep that a secret.   I adore him so much it hurts. He is super good to me and lets me take his charge cards and buy whatever I want. He takes me out to dinners, movies and we spend so much time together that it makes me wants him so bad.

One day while he was at work I used his Mac and I saw a file called AJ.  Of course, I HAD to see what was in it. I thought it might be my school records and stuff. It wasn’t though, it was photo’s of yours truly. Not dirty but just so many of me at pool, at dinner, at volley ball. It made me start to think that he felt the same way about me. The more I thought about it the hotter and wetter my little pussy got. I closed everything and went to my room. I laid on the bed thinking of him and started cupping my little boobs. It felt so good and I was aching to feel more. I put my fingers inside my panties and started to finger my creamy teen pussy. I was almost over the edge when I heard him coming up the stairs. I quickly took my hand out of panties and told him to come in. He asked me if I was okay as my face looked flushed.   He put his hand on my face to see if it was warm.  He kissed my hand and said dinner would be early as he had plans.  I wondered if he tasted my juices on my hand.

We had dinner and we were both pretty quiet. I went up to my room to finish my assignments. I could hear him talking but not loud enough to make out exactly what he was saying. I picked up the phone and quietly listened. He had called to get an escort. No, he can’t do that I was so upset and jealous. I listened more as he asked for a girl that fit my description exactly. I had to stop this as he is mine.  I changed to my uniform from last year.  It was a little to small but perfect for what I heard him ask for.  I put on black lace panties and a pair of fishnets. I had some patent heels and was ready to face him.

I knocked on his office door and without looking up he told me to come in. He asked me if I had plans for the night with friends and I told him no. He finally looked but at me. He looked surprised but I could tell my hot teen body in my much too small uniform made him excited.  “AJ, why are you dressed like that”, he asked. I confessed it all.  I told him I heard his phone call and that I was upset and jealous. I told him I was playing with my dripping pussy after seeing my folders on his Mac. I was talking so fast he told me to calm down and put his arms out for me. I fell in his arms as he tilted my head to kiss me. Not like a brother kiss but like the way a man and woman kiss before they fuck. He told me he will cancel but then I have to do all the things she would have to satisfy him. I stood in front of him and did a slow, sensual strip. I walked slowly to him and unzipped his pants. He pushed me down to my knees and I held his cock in my hand and started licking and sucking it. It was so wet that drool started running down my chin to my little tits. He groaned and pulled me up. He picked me up and sat me on his deck. I wrapped my legs around him as he pushed his big, hard cock in me. He picked me up off the desk as he fucked me harder and harder. His mouth hard on mine as he popped my cherry and shot his load in me.  He looked at me and told me we had all night as he took my hand and led me to his big king size bed.

The Slumber Party

There is a slumber party at your house for all of the prettiest girls at school. We have been giggling and running around your house. Finally, you told us to go to sleep.

I toss and turn in my sleeping bag on the floor of your family room. I just can’t seem to fall asleep, even though all the other girls have. I remember at home, Daddy always brings me a glass of water into me when I can’t sleep.

Thinking a glass of water is the key to sleep, I walk into the kitchen. You find me standing in your kitchen looking so cute. You help me with my glass of water and I ask if I can sit with you until I am sleepy.

You hesitate but decide that seems harmless. I look so innocent and cute in my pink pajamas. I follow you into the living room. You are kind of surprised when I place my head right in your lap. You can’t help yourself!  Your cock immediately gets hard.

You blush and are just about to send me back to my sleeping bag when I ask if I can see that cock in your pants.  I start kissing on the front of your jeans and my little pink nightgown hits the floor before you can utter a word. Your head is still spinning, you think you should stop at me, but you don’t.

Miley

Date with Uncle Jimmy

I have a special date tonight.  I call him Uncle Jimmy because he has been my daddy’s closest friend ever since I can remember. He really isn’t my Uncle.  He is the hottest man I know and even all my friends think so. They ask me how I can stand being so close to him and keeping my hands off. It isn’t easy

He is taking me out to dinner tonight. I know he doesn’t think of it as a date but more like spending time with his little sweet girl. Tonight he will see I am not so sweet and just how dirty I can be for him. I put on my shortest little skirt and a tank top that barely fits my budding little boobies. No panties, giggles! A pair of boots, and of course lots of lip gloss to accentuate my full cock sucking lips.

I jump up and give Uncle Jimmy a big hug, by now he can tell I have on no panties.  He looks surprised at how gown up I look and I can tell he is getting horny looking at me. We talk the whole way to Red Lobster and he teases me when I call this a date.  I am not really hungry and he lets me sip on his Crown and seven. It makes me feel really good and really daring. I put my hand on his leg and look up at him and smile. He doesn’t take my cute, soft hand away as I move it to his crotch. He is rock hard and ready to leave.

We drive for awhile and he suggests we pull off road and talk.  Talk? Sure I bet that is what he wants to do. He pushes his seat back and I take off my tank top showing him my perfect teen boobies. He tells me how sexy I am but that we should not do this. I promise him I won’t tell anyone as I unzip him and take out his big, thick hard throbbing cock.  He pushes my head down and I lick and suck his cock. I go really slow because I don’t want him to cum in my mouth.  Not like I don’t love wet, sticky hot jizz spurting down my throat but I want him to cum somewhere else.  His finger starts to play with my hot creamy teen pussy and he tells me how much he wants to fuck me. He is afraid I will get pregnant. I promise him that if I do I ill blame it on a boy I started to see for just this reason.

I lean back against the seat and tell him I want him to be on top.  He wants me so bad he doesn’t ask why. Soon he is pounding my hot teen slit as I wrap my legs around him tight. He tells me he better pull out but I just wrap my long firm legs around him tighter and tell him no.  He knows what I want and that he is only one I want to get it from.  I am about to cum I can feel my body tighten as I yell ” Give me your baby batter, knock me up and give me a baby”. He cums so hard and I make him lay on me to make sure his swimmers find my baby making eggs.  I can’t wait.

Punishment Time

I come home from school and it looks like I am in trouble again. He is sitting in the den looking very stern. My report card was emailed to him and it is very bad. I can tell this might be one of the worst punishments ever.

Phone sex daddy tells me to slowly strip off all my clothes. This is so humiliating. I try to cover my boobies and kitty with my hand but he slaps my hands away.  He makes me bend over and spread my ass cheeks. He then makes me get on my knees and suck his cock  till my eyes water and I gag.  Phone sex daddy takes me over his knee and spanks me hard till I cry. I can feel his cock still hard from me sucking it. He pushes his finger in my tight little pucker and it hurts.

We go up the stairs with my hand holding his big hard cock. I know what is about to happen and I cry and scream, please no, please no! He makes me go into the bathroom and get the enema ready.  I am crying and pleading but he doesn’t care. He puts Ben Gay all over the nozzle and slides it into my little pucker. I bet him to let me release it. Finally he lets me but he watches me the whole time.

He makes me put the punishment condom on his big thick cock. I am crying so hard I am shaking. Phone sex daddy puts on the nipple clamps so tight I scream. It is almost over, I go to a happy place in my mind a place he can’t hurt me.  He bends me over the bed and slams his cock inside my tight little bum. I have learned how to make him cum quick. I yell while he is fucking me ” Fuck me, fuck me and hurt my tight little girl asshole”  He finishes, zips up and tells me to clean myself up before everyone else gets home.

Fat Piggy Piggy, Oink Oink

Giggles!  I am so happy that an older real Mistress has asked me to take care of her Little Boy. Giggles, little boy really isn’t little or young. I call him Oinker, or Shit Piggy or Piggy Piggy, Oink Oink. You would not believe the things I did to his big, fat flabby ass. He cried like a little baby piggy when I made him shove the Ben Gay covered butt plug in his Piggy ass.  I tried not to laugh, but I ended up laughing so hard I got the hiccups.

If you can even imagine this I made him eat bowls and bowls of wet dog food.  Maybe I needed Piggy food for him. I was having so much fun at his expensive I just started coming up with mean and painful things for him to do to himself. ROFLMFAO!  By the time we were done he was begging for more. I have more prepared for next time.

I will make him drink gallons of water and lots of beer.  I will make him rub Ben Gay in his pee pee hole and just let him dribble a little drop at a time. OUCH! You know that is going to hurt. I hope some friends come to hang with me because they will just love this! See you soon Piggy Piggy fat fat.

Santa’s Little Helper

Are you ready to be my Naughty Santa? He was standing by the tree putting his sack of  presents down. I walked behind him reaching my hands around him rubbing his velvety pants. I’m gonna show him what a good girl I’ve really been. Pulling his cock free from his pants. Wrapping my little hands around his cock. He whispered to me that all the good girls get the best gifts. He turned around and I started kissing the tip of Santa’s cock along with a few licks. He held my head still while he pumped his huge cock down my throat. The cum was dripping down my face like a good girl. He was still hard and still had one more special gift for me. He sat down in my Daddy’s favorite chair as I undressed for him. Climbing onto his lap he bounced me up and down telling me to be a good girl and cream all over his cock.

My Step-Daddy has been dressing up as Santa since I was a little girl. Every year he makes the holidays so magical.

Love Always,

Zoe

xoxo

Dear Santa

Dear Santa,

I have been kind of a bad girl this year. Will you still bring me my presents?

I love you, Santa. Remember that sweet little thong you brought me last year? I woke up Christmas morning, and I found it under my pillow! They are still my favorite pair of panties!

If you come to my house to bring me my presents, please come in my bedroom.  You can wake me up this time. I promise to make you feel very good. You will be tired by the time you get to my house, you can crawl into bed with me and take a sexy nap with me, just like my special sexy Daddy does.

Please bring me lots of presents Santa!  Love, Miley

Introducing Cami

I know I have used the beautiful Cami in a few of my blogs. I think it is time I introduced her to those who have asked. Cami was my first female lover when I was about 15. I went to school with her, her brother and many of her cousins. Looks wise one was hotter than the next. She had long hair  down to her perfect ass. Killer green eyes, slim with 32b tits and legs that could crush a walnut when wrapped around you. They all looked alike yet different. Cami was a strawberry blonde, and her brother a ginger. Some of the cousins had black hair so you see, there was a an Adair for everyone’s personal taste. My lust crush was on her brother but things can surprise you in the sexiest of ways.

We became very close friends when we both wanted the same boy. He was playing us both and when we found out he was kicked to the curb and we became the hot best friends everyone wanted to fuck. She invited me to spend he night at her house. It was a huge house that we were all in awe of a Victorian type mansion. I thought this would be my chance to get close to her older brother Peter.

Her room was beautiful. Candles were everywhere with soft English Ivy bedding. She even had a dressing room with mirrors on every wall. We had dinner and went to her room to listen to music. Cami gave me an E pill and I started to feel so good and so fucking horny. I asked her about Peter but she told me he would not be home tonight. I must have looked really disappointed so she hugged me tight. She smelled so fucking good. I felt lost in her long silky hair. She started slowly moving to Season of the Witch. It was such a sexy old song to dance to. I started dancing with her as she came behind me my ass against her pussy as we slowly moved. I was started to feel things I had never felt before. I was wondering what her body would feel like pressed against mine, wondering what her pussy would feel like…Mmmmmmm and our tongues mingling together as we rubbed our wet slits together till we both came. The song was over and she grabbed my hand and we jumped on her bed.

She told me she she had secrets she wanted to share with me. She opened her night stand to show me the secrets. In there was a double  headed dildo, anal beads, nipple clamps and all sorts of Kama Sutra oils and candles. I have never seem so many mysterious things in my 15 years. She pushed me down on the bed and started to kiss me. Her kisses tasted like sweet cherries. Her soft hands started removing my clothes. I was so wet, I wanted her so fucking bad. She started to kiss my nipples, the kisses soon turned to bites. Then she put on the clamps. It was just unreal the sensation. She kissed down my teen body with me aching to feel her soft tongue on my pussy. She poured on some oil making my whole pink pussy tingle. She licked and sucks till I gushed juice all over her beautiful face. Tonight I knew I was going to let her take the whole lead with this being my first time with a girl. She straddled my face telling me just how she wanted her pussy eaten, she tasted like honey and I wanted every drop. I grabbed her ass and pulled her down hard on my face with my tongue fucking her till she came.

She got off of me and with an evil smile got the doubled headed dildo. She pushed one end into my hot wet pussy and the other into hers. She rode me with the dildo pushing in and out. I sat up and wrapped my legs around her and took her perky beautiful tits in my hand. She put some mysterious scented lube on her finger and pushed it in my tight ass. I felt a tingling, hot and numbing sensation all at once. I sucked her nipples as we both fucked each other hard till I heard her moaning and she started going faster with her finger and dildo. We both came in hot burst of wetness. She pulled out of me and we kissed for hours cuming over and over again rubbing against each other.

So now you have the whole story. Boyfriends came and went, some we shared but always as a three-some. We were together till she moved away. I did learn a few tricks and she was more than happy to let me take the lead on many nights together.

Blackmail 101

It is the last week before Christmas vacation. My teacher said he needed to have a talk with me on Monday. I have a very bad feeling about what that means.I know my grades have really sucked lately and there is no way I am going to do extra credit on my vacation.  My friends and I have all told stories so we can go on a ski trip with the college boys we met last week. My daddy will believe just about any thing I tell him. I am his very special little princess. I have a plan for Monday.

I am going to wear my shortest skirt and a way to small sweater. I am going to hop up Mr Jake’s desk while he tries to tell me I am failing and that I need to apply myself and catch up during vacation. I will wear loads of shiny strawberry lip gloss which makes my lips look so amazing and full while I suck on my finger and stare down at his crotch. Before he can stop me I will get down on my pretty little knees and unzip his pants. As I look up at him with my sweet little face I will lick, and kiss and suck his cock like he has never felt before. I am the best little cock sucker ever! Only thing is he might want it every day and I am way to busy for that so…..I will have my phone on and my bestie will have the whole thing to blackmail him with. I guess I will be getting excellent grades the rest of the year!