Growing up, my parents were gone a lot. They both had busy careers, and both of them traveled for business frequently so over the course of years, I had three different nannies. My favorite one was Tom.
Tom was really funny and silly. He made me the best chocolate chip banana pancakes and would play all sorts of games I made up to entertain me. But my favorite memories of him were our sexy bath times.
One night, it was getting late and Tom told me to start getting ready for bed. He drew me a bath while I brushed my teeth, and as I stood there watching him leaning over the tub, squirting bubbles into the water, I started to feel funny between my legs. I rinsed my mouth out and took my clothes off as Tom stood up and turned to face me. He immediately looked away, but then his eyes moved back to me. My breasts were developing, and a tiny bit of hair had sprouted on my pussy. It was like he wanted to look but didn’t think he should. I was between him and the door, and an awkward silence filled the air.
“Um… ok, excuse me,” Tom said as he started trying to get around me and leave.
“No, wait… would you please stay with me?”
Tom kept his eyes on the floor. “Annaliese, I should go. This is inappropriate.”
The funny feeling between my legs had become more intense. I noticed Tom had a big bulge in the front of his pants.
I stepped into the tub, laid back and spread my legs.
Tom couldn’t avert his eyes any longer. He stared at my teen pussy with the strangest look on his face. I slid my hand between my legs and said, “let’s play a new game.”
‘Sexy Bath Time’ became my favorite of all the games Tom played with me. 🙂
Archive for the 'Underage Roleplay' Category
Page 35 of 42
As if it isn’t wonderful enough being a Klassy Kat girl and working for the Klassiest phone sex company there is the callers are just awesome! Where else would a gentlemen ask me if I would take a bath for him? Imagine how relaxing it is taking a hot bubble bath in the middle of the afternoon and bringing him with me. Those fragrant bubbles feel amazing on my skin and hearing him cum just pushes me over the edge. Maybe I will tell you more about him another time but today it is all about my Johnny.
The first time I met him I could tell he was fascinated by me. What an adorable little guy he was too. He would stare at me and didn’t care who noticed. Soon we began to play a fun little game that slowly became very taboo. It was always shoes off at my house so when he forget I would make him be a good boy and take them off and his punishment was for me to tickle his little feet. He would laugh and laugh and well, I noticed he would also get a little boner.
It wasn’t long before he was putting his feet in my tan, soft manicured hands. He loved the tickling and so did I. He was way to adorable to resist. One afternoon I was visiting with his parents and we were in the kitchen having espresso. Little Johnny was sitting as close to me as possible. He kept putting his little feet in my hands to tickle. His mom and dad thought it was hysterical and had on idea my Johnny had a little boner. I whispered in his ear that he was going to get a little surprise he didn’t expect if he wouldn’t stop. As his dad chatted away and his mom had her back to us sprinkling powered sugar on the Pandoro I slipped my hand in Johnny’s shorts. He let out a little yelp as I wrapped my hand around the his little boner and started to stoke it.
His mom can back to the table and as we drank our espresso and ate our Pandoro I kept playing with Johnny and teasing him. I whispered in his little ear such dirty things. The whole time his parents talked I stroked his cock in my tan hand. Sometimes Johnny would look down and stare at my watch with it’s band shining under the bright kitchen light. When we were finished he took my napkin with the lipstick print when no one was looking and ran off to his room. Before he grew up and went off to college Johnny and I had many naughty memories.
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 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.
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
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.
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.
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.
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,
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
