Stories from days past, you can find masterposts for series here about older stories, you can also post your favorite older stories here as well, be sure to credit the author.
More Stories wrote:
Jacked Off by the Babysitter by More Stories
When I was a teen my little brother and I had a babysitter watch after us when my parents went out. I personally felt like I was too old to have a babysitter, but since I was known for being a troublemaker, and I was stuck with a younger brother (11) too I was condemned to being babysat even at my age. Fortunately, we had a hot looking babysitter named Nancy, who was 18 with big firm boobies, green eyes and beautiful auburn hair. In front of my parents she always acted all calm and proper, but when my parents weren’t home she was a very different person. She would let us do a lot of things that my parents would never approve of like stay up and watching grown up programs on cable that had bad words and nudity, eat junk food, and even teach us dirty words. She knew I was a horny little devil and liked to tease me in different ways.
One night when babysitting us we were playing cops and robbers with my little brother to entertain him. We would take turns, one person being the policeman, and the other being the robber wearing a ski mask. We used the whole house, and with the lights off the robber would have to sneak into rooms and steal stuff putting it in a pillowcase without being caught. The police person would go through the house one room at a time looking for the robber. If you didn’t listen, and hide really good the policeman could find you and arrest you. We had these cheap handcuffs that were actually made from metal, but had a little hidden safety latch on them. Funny thing is it was really hard to reach the release latch if you were the one handcuffed.
One of the times when I was playing the policeman, and she was the robber, I caught her in the den hiding behind the couch. I got to arrest her and “play” search her for anything hidden on her or in her pockets. She let me reach under her shirt and feel her breast through her bra, and reach into her jeans pockets. I even tried to unbutton her pants and got as far as unbuttoning and unzipping them before she stopped me saying that was far enough. Seeing the top of her little white panties with a red elastic waistband and little colored dots on them made me really horny. Her smooth skin and flat tummy drove me wild. I wanted to do more but she would not let me.
We had been playing for a while so around 9:30 she told my brother it was bedtime. He didn’t want to go to bed and was being a brat about it. She ordered him to get into his pajamas, but said I could stay up longer. She put my brother to bed, and I went to change. She was sitting on the couch watching TV when I came out a while later in my lose-fitting pj’s with stripes on them. As soon as she saw me she started laughing poking fun at my pajamas. Feeling belittled I threw a fit and jumped on her trying to overpower her. I was trying to pin her down to the couch but she was stronger. In all the struggling and wriggling around together I got excited. I wasn’t wearing any underwear and with all the close contact I got a raging hard-on in my pants. Then she rolled me over on my stomach and managed to handcuff my arms behind my back! With my hands behind me I could not reach the little release catch. I was stuck handcuffed with a hard-on grinding against the ground now! I mean it got rock hard. She said she was going to spank me like a little baby if I kept misbehaving. I didn’t care. Then things got even worse (or better depending on how you look at it). When she rolled me over again to talk to me the head of my erect penis popped out of my pajama fly! I was so embarrassed that my face became hot. She stared wide-eyed at my helpless twitching penis as I lay there powerless to do anything and reached down and grabbed it by the shaft. I guess I have a pretty big dick for my age and she seemed to be very impressed with it. “Oh my!” she said with a sly tone in her voice. “Well we are a very bad boy aren’t we?” I was really embarrassed but really turned on too at the same time and just stood there speechless. Forcefully she pulled me over her lap on the couch with my shoulders propped up on the end of the couch. She pulled my pj pants all the way down and reaching underneath she started stroking my super hard dick with one hand, while spanking my naked butt with the other. “Bad boy!” she kept playfully saying while she lightly spanked my butt and stroked my dick. My dickhead now got wet with precum that she used as lube to stroke me ever further. She spanked and stroked me as I moaned in ecstasy till I arched my back and jutted my hips forward spurting all over the couch pillow! I was really embarrassed after, lying there handcuffed and bottomless with spooge all over me & the couch. She made me promise to not ever say anything about it or she would never baby sit for me again. I eagerly agreed. The she cleaned the couch off and flipped the cushion and told me I needed to go to bed.
Janienudiepants wrote:
Babysitter by Janienudiepants
Very nice story. I babysat a lot for my mom's divorced friends as a teen. Mainly single moms, occasionally everyone else. I dreaded some kids, and others I lived to die for, they were so cute. One pair of boys were four and seven, a bit like you, and cute as h*ll. At bedtime one thing you knew for sure who had a "hard-on." Their little flagpoles stood out of their pj tents once they found the hole. Of course, little boys button pjs have a huge hole in front -- they never button them, and their little d*cks found it all the time in tickle fights, wrestling playing around with them before bed or just sitting with me snuggled up watching TV. I grew up with the impression boys always had a hard-on.
I always enjoyed the cute little kids and what I saw. I imagine their mom played with them like I did. They weren't shy pulling each others pj bottoms down at all -- it was all great fun. They had such cute bottoms! And of course, they shouted with glee whenever they could pull something down from me!