My AMAZING babysitter and I have some “play-time”!!
My Favorite Babysitter Ever
My name is Andy, I am 5’11”, have sapphire eyes, and technically I am sixteen because I still got a few months to go. This great, and true story, happened when I was 13 and just starting
to understand the addiction to the pleasures of masturbation. When I was little, around six or seven, I was too short for my age and my mom put me on hormonal treatment. I grew taller
and so did something else. My penis, when I measured it when I turned ten, was about eight and a half inches. My best friend loved it, but, that is for another time.
When I turned eleven, however, Mom took me off the pills because she later saw that it was pulling a double whopper (no pun intended) on me, I quickly grew to 4’3″. I was
still short for my age but Mom would have none of what was happening down below. Whenever I got an erection, she would see it and tell me that it looks like I need to go
to the bathroom. In that same year, when I started middle school, Mom got promoted to head RN and had to hire a babysitter to watch me for her new schedule. Anna, my new babysitter, was beautiful.
She had brown hair with blonde highlights, was about a foot and a half taller than me, had the purest emerald eyes and was about to turn eighteen. I knew this because when my Mom laid her resume on
the table and walked away, she was born the same day I was. I could tell immediately Mom loved her and soon so did I. She would have a suprise for me today and so our story begans….
It was midsummer, and unseasonably mild temperature for a day such as today. Mom got a call around 9:32 am, waking both of us up. While she talked medical mumbo-jumbo, I got made my bed and
went to the bathroom to knock the dew of the old daffodill. I made myself some toast and started the coffee for Mom. Wilst the toasting was nearing golden-brown prefection, I poured myself a
mug full of OJ. After my morning routine was nearing completion, Mom came out with her usual stressed out face on. She said, “Good Morning, Sweetie,” kissed me on the head, and waited for the person
on the phone to stop talking. While waiting, she thanked me for making coffee and sat beside me at the dining room table. She asked me, “Honey, is it okay with you if I go in to see what they so want with me?”
I nodded and in reply asked a question of my own, “Could Anna watch me again?” She gave the same notion of agreement and said to the person on the phone, “I will be right in about in hour, Okay?” She got up, kissed me
on my forehead and said walking back into her bedroom, “I’m sorry, honey,” and when she made it to her destination, she closed the door. We lived about a half an hour out of the hustle and bustle of the city with
plenty of wooded area for me to explore. She came out with a towel on her shoulder and went into the bathroom, and less than a minute later I heard the shower start. I know Mom meant well, after all being married to a real
asshole that couldn’t keep his hands off of anybody (including me) had dragged her to become a great single parent with all the stress attached.
In less than ten minutes later, the shower stopped and the stress mask she was wearing just a few minutes ago seemed to have rinsed off. Even without makeup she looked great. She picked up the phone and said, “I’ll call Anna to see if she would care
to watch you until I get back,” I replied with an enthusiastic thank you. She flashed the smile that could light up the entire city and I smiled right on back. She went again to her bedroom and finished titivating. I walked into our
den and grabbed my book, Artemis Fowl The Arctic Incident. I was finishing the eighth chapter when Mom came out happier and beautiful as usual. She said, “Anna says she doesn’t have anything to do because all her pals are away somewhere
and is coming and she’s fifteen minutes away, but, I have to go, Sweetie, OK?”
I asked, “When are going to get back?”
“I will call or if I am really swamped, about midnight or one thirty, but, I want you in bed before eleven, OK?”
“Don’t give me that depressed look, it won’t work on me this time. Just promise me you will be showered, teeth brushed, and in bed before eleven thirty.”
“Thank you,” she came over, gave me a big motherly hug and kissed me good-bye. Laying my book down, I followed her out the door. When she got into the car and started it up, she yelled, “Love you!” Instead of yelling, I did the sign language
way and she did the same.
Not more than two minutes later, pulls up Anna in her car. I was reading, I knew she pulled up, and knew it would be seconds before she walked inside. She walked layed her bag down with what sounded like a thud, and came over and picked me up and gave me a huge squeezing
those C cups into my chest, and said, “Hey Squirt, where’s Mom?” Ever since she was hired she called my Mom, Mom, like she was related or something and in a strange way I could see some resemblances.
Answering,”She got called in again, and said she would call if she was coming home early. If not, she said it would probably be late when she would get home.”
“So you bedtime is…?”
“OK. So what are you going to do today, seeing as it is only about ten o’clock?”
“Do you mind if I go exploring again?”
“Sure, but, stay close.”
“Yes ma’am,” grudingly answering her.
In one swift move, she grabbed the remote, turned on soap operas (YUCK!!), and landed safely on the sofa. While she was doing her acrobatics, I ran into my bedroom grabbed my laptop, which was given to me by Mom last year for me to I guess explore my sexuality, my air card, and finally made my way
to the door. Just as I was about to walk out the door I saw something in bag, I put my supplies down and picked up what looked to be a purple penis about the same size as my own but about two inches thicker. When she saw me, she pretty much screamed, “Stay the hell away from that!!” I dropped it in her bag and bolted with my supplies out the door.
It was peaceful in our backyard, but to me, it wasn’t woody enough (again no pun intended). I had a secret hiding spot in the woods, a derlict wooden lean-to, which if not looked at the right angle, you could walk right into it or past it. It was a place where I could be naked to my heart’s content and nobody could ever see me.
It was a place where I could masturbate out in the open and not get caught. It was about a ten to fifteen minute walk from the house.
The year before, also before my birthday surprise of a laptop, my best friend and I would jerk each other off and watched some twink porn (my friend and I’s favorite). His brother gave him his porn passwords before he left for college, which opened a new way
of sexual excitement for us. We didn’t do anything to serious except some sucking each others dicks (usually at the same time), butthole licking, and a fingering or two. We could cum and we could have multiple orgasms and cum soakings (We still do this today but have not had anal sex yet but thinking about it and we are totally straight).
He gave me a password to some of the best masturbating twink porn yet. It was supposedly a pre-birthday gift. This is for another time back to our story…
When I came to “Nude Shack”, I stripped almost immediately. My penis was rising and it was getting hard fast. I barely made it. It saluted the sun and the air around me. I layed my clothes by the entrance and then went out and layed on the moss covered ground. It felt great to be naked and free. The only thing casting a shadow was my penis.
My anxious “joystick” was almost begging to be pleased, but, I tortured it some more by flipping over and rubbing it against the dew soaked moss.I gasped at the sensitivity of my friend.
I returned to my “playground” and booted up my computer. The best thing about Mom working is, she never gets to look at my files. I plugged in my air card and then went back outside to enjoy the heat from the sun on my preteen nude body.
When I heard the Internet chimes, I walked slowly back into my playground. My porn homepage was already set up and signing itself on for me.
There was a movie I just loved to watch and masturbate to. It was a twink movie with four twinks, two sets of twins, and the twins were brothers.They looked like my friend and me jacking off a clone of each other. They sat “Indian style”, just like was sitting but on wooden floor instead of carpet, and almost immediately grabbed the other one’s penis and slowly started to stroke them.
I soon was in sync with them. Not more than two minutes and each of them were moaning with their own form of ecstacy. I was slowly starting to do the same. In my mind’s eye, I changed them into my schoolmates’ faces who were also twins. Their names were Dylan and Cole Sprouse. I loved their bodies and I was able to see their penises when we took showers after P.E. For some strange and eerie
reason whenever I was in the showers with them, they always became hard and they would, one at a time, stare at me from head to toe or the other way around. I, occasionally, did the same when they were not looking at me.
I heard the boards creak by the entrance and thought, “I am soooo dead. I am dead.”
As I turned, I felt like I was about to cum right then and there. Anna was staring with mouth wide open. The only sounds were the moaning from the twins on screen. My precum soaked hand was still slowly stroking it’s target.
Anna was the first to break the silence, “I have watched you come here but didn’t know what you were up to. So this is what you have been doing…?” All I could do was swallow in perhaps an effort to move my fast pacing heart back into my chest. I stayed speechless.
She again was the first to make a move, this time for real. She walked up to me and kissed me on the lips. It felt great, so I kissed back. After a few seconds, she pulled away, but still in arms reach. SHe knelt down this time, picked me up off the ground, started stroking my precum soaked cock real slow, like I was just doing. With her hand across my back and to my butt crack she slowly started
to tickle me there. Once she noticed I was liking it, she planted those velvety lips back on to my own, but, this time she slyly pushed her soft tongue onto my own. I felt like I was in love. With her stroking, tickling, and kissing me, I decided to make my move and slowly took my hands and unbuttoned her plaid short-sleeved shirt. If she noticed what I was doing, she sure showed no interest. When I was able to touch her bra, I started squeezing her breasts
through the bra. She the started moaning and soon so did I. I stretched my legs to the floor and since they were asleep, I fell right down without her. She snickered a little and finished what I had started. She took off her shirt for me to look at her green camo bra. She then took off her jeans, that went only to her ankles, very slowly as to torture me. When they were off, they revealed a pair of
matching panties to her bra.
Right then like her acrobatics before, took both bra and panties off in one smooth move. I was still speechless. She was shaven but looked to be dripping and her nipples were like pink eraser tops and were already erect.
She then came back over and sat her wet pussy on top of my penis. “You have one big cock for your age and WOW is it thick,” telling me as she moved up and down on my member.
All I could say was a soft thank you as my body quivered with pleasure. She pushed down atop of my shoulders and leaned into tongue-tie with me once again. She continued to grind her smooth yet dripping wet pussy on my cock
As we were getting back into our original stimulating make out session, I saw her hand reach over to her jeans and pull out the purple dick I saw earlier.
I then saw it disappear from sight as she took it behind her back, thinking nothing of what I just saw. I closed my eyes and felt like I was in heaven, when all of the sudden I felt an intense sharp pain in butthole. I felt as if I was bleeding and she got off of me. I started to cry. When I moved my legs apart, it did, however, relieve some of my agony.
I tried to reach down to take it out but she came up to my face and whispered, “Let me turn it on first, baby.” I stopped my movements as she moved to where it hurt the most and I heard something turn on with a soft click, and that something started to vibrate in my butt.
She noticed I grimaced at it, so she turned it up some more. It was relieving some of the pain. She must have noticed I was starting to enjoy it because again she turned it up. It started feeling great.
She made her way back up to my face when she stopped half way. She started to kiss and softly bite on my sensitive nipples. She kissed her way down to my slowly softening penis. Her soft lips touched almost ever part of my overly sensitive body.
She then took it in her hands and slowly stroked it like before but massaged my balls into circles. I closed my eyes once more and fell into complete ecstacy. I started to moan softly.
I then noticed a new sensation in that area, it felt better than ever before. I opened up my eyes to first feel and thensee she was using her soft, warm mouth to drive me even closer to heaven. I was starting to moan a bit louder.
A few minutes later it felt like my time in heaven was ending as my balls started to boil. I told her, “I think I am going to cum,” but, all I could do was moan ever louder and louder as she continued to stroke my tube steak and massaged my red hot balls. This time she started to, while my cock was still in her silky warm mouth, she circled my cock’s head with her soft tongue.
I couldn’t take the pressure any longer and told her,” I am cumming nooooooow!! Oh my gooooodneeeeeesss!!”
She kept bobbing her head and I could feel my cum shooting up my dick and then I came so damn hard I didn’t know when I was going to stop, but unfortunately, it did. I heard a loud gulp and could tell what was happening.
She came up to my lips and kissed me so I could get a taste of me own seed. It tasted ok, just a bit salty. We made out for what seemed like an eternity and I felt the same feeling again. I told once more, “I think I am cumming again…Ooooh!!”
With her kissing me and that fake dick in me vibrating my insides, I came again. We stopped kissing and watched the show. I came with atleast six ropes but it looked like a miniture fountain going off and it felt unbelievable. Some of it landed it on my stomach and chest, but the majority landed in between her beautiful breasts.
When the she sat up, my cum streamed down to her still wet pussy and finally to the floor between her knees and pussy. She, without turning it off, took the purple penis from my butt with the sound of a pop.
I could still feel my butthole still vibrating and gaping wide open, I whispered to the goddess who brought me to cumming twice in a row ,”I love you, Anna.”
She, sitting up and me still laying down with my legs spread wide, with a whispering voice said as she dangled the purple dick in her hand, “I love you, too, Precious. My turn?”