Babysitting Fun.

When I was a teen, I used to babysit two neighborhood boys who lived 2 doors down the street. I had been their sitter for about two years of so when things got a little kinky, you might say.

We all used to play games and wrestle around in the floor while watching TV and stuff like that. Jimmy was the youngest boy at 9 and his brother Tony was 12. We were all in a pile in the floor wrestling around and giggling, when I realized that the older boy Tony, was beginning to help himself to a free feel of my boobs and my ass. I was almost 17 at the time and had a nice tight teen body with 34C boobs.

At one point, I climbed on top of Tony and sat across his waist pinning his shoulders to the floor. I was squirming around telling him to say "uncle" and I'd let him up. Then I realized that his little cock was hard and pressing against my ass. I continued to squirm around grinding against his hard cock,

Finally, he cried "Uncle" and I roll offed and the three of us just laid back on the floor laughing. Then Jimmy shouted " Look, Tony has a boner, Tony has a boner" teasing him and sure enough his little had cock was bulging in his white briefs. Tony looked down at his bulge and got up and ran into his room as Jimmy laughed away.

I felt sorry for Tony, he was a sweet kid and I knew he was so embarrassed. I told Jimmy it was time for his shower and I walked him down the hall and after I heard the water running I went across the hall to their bedroom.

I knocked on the door then opened it slightly, Tony was lying on the bed face down. "Go away" Tony shouted. I went on in and sat on the bed with him. I leaned down and told him not to be embarrassed, I rubbed his back and ran my hands up and down his legs and he rolled over. " You shouldn't be embarrassed, I bet you have a really big cock" I whispered and he smiled sheepishly. "Are you all hairy" I whispered and he said "Just a little". "I'd love to see it" I whispered, and I pulled down his briefs and his hard little cock was not so little now, pulsing and growing hard in my hand. And I was surprised at how hairy he was at that age as I watched his cock grow.

I again, complimented him on how big he was and he was just frozen in place as I pulled my T-shirt over my head exposing my braless round boobs. I put his hands on my boobs and as he rubbed them, I took his hard cock in my hands and stroked it slowly. In just a minute or two, Tony's had cock throbbed in my hand and 2-3 squirts of cum shot out as he gasped and squirmed.

I heard the water in the shower shut off and I told Tony to get dressed. As he pulled up his briefs, a few drops of cum oozed out. Tony hugged me and asked me if I'd be his girlfriend. I told him I would, if he could keep this a secret and he grinned and said " I promise".

For the next year or so , I was Tony's sex teacher, I wound up letting him fuck me a few times among other things. After that I went away to college, and he used to write me love letters and tell me about his new GF. I hope she appreciated all that I had taught him. LOL.

Comments

Anonymous

by Anonymous on Sep 11, 2022 at 2:51 PM

My older cousin Bobby was about 15-16 and would watch my little brother and I when we were 11-12, when my parents went out for the evening. He used to bring over porn hidden in a sports illustrated or Hot Rod magazine, We started taking turns jerking off each other's dicks and eventually after a few weeks we were sucking each other's dicks. My little brother had his first wet cum in my mouth. Only a few drops, but he felt like a stud after that. LOL.

(5)  (0)
Anonymous

by Anonymous on Sep 11, 2022 at 6:23 PM

From the male perspective, I had a similar experience. A girl who was 17 and live a few houses up was our babysitter every other Friday when my parents had their bowling league. I was in 7th grade at the time and had no concept of what alcohol did, but in hindsight I realized that she was drinking my parents booze when she would babysit. One night she had served herself quite well and she was bragging to me about how good she was at blowjobs. I sheepishly told her that I had never had one (I wasnt 100% sure what it even was) and she told me she would give me the best one ever. I sat on the couch, she knelt between my legs and pulled my shorts down. Her lips wrapped around my cock and the warm, wet tickle of her tongue running along the bottom of my dick was all it took. I only lasted long enough for her mouth to reach the base of my dick and she held her head there as I shot down her throat.
When I was done she said "I told you im good." I dont think she remebers that night... never happened again.

(22)  (0)
Anonymous

by Anonymous on Sep 24, 2022 at 10:41 AM

You're so fucking kind, I wish something of like that ever happened to me

(1)  (0)
Anonymous

by Anonymous on Oct 1, 2022 at 4:42 PM

That is a great story, Jeannie!

I had a similar experience when I was 13. My mother's friend came by to stay for a long weekend with her 18 year old daughter. That night (a Friday), they decided to go out on the town together, planning to return the following day, leaving the daughter to "babysit" me. The daughter was pretty with round breasts and a nice ass and legs, so I didn't mind, though I pretended to be insulted about having a "Baby" sitter.

After they left, we hung out, chatting about various things. Horny kid that I was, I couldn't keep my eyes off of her and she noticed. After dinner, she told me I needed to take a shower, so she stood by as I took off my clothes in the bathroom. As I showered, she stayed in the bathroom, having a casual conversation with me. When I was done, she held the towel and dried me off, paying special attention to my crotch and ass. She smiled as my cock got hard as she held it through the towel. Then she told me to go to bed!

I tried, but could not sleep at all. My mind was racing with all sorts of horny thoughts as I stroked my hard cock. Very frustrating. I decided to see what my "babysitter" was doing, so I tip-toed to the living room. The only light was from the tv. I saw her on the couch, wearing only a tee shirt and panties, her legs open, rubbing her pussy and squeezing her breasts. I was fascinated. I held my hard cock as I watched her. Suddenly, she turned her head in my direction. I quickly ran and jumped into my bed.

A few minutes later, she came into my room, still in her tee shirt and panties. I pretended to be asleep as she walked slowly around the bed. The light from the street illuminated her. She pulled down the cover and saw that I was naked with a hardon. She took hold of it and stroked it. There was no longer any point in pretending that I was asleep. She said "You better not tell." With that, she took her shirt off, revealing her beautiful round breasts. As she sucked me off, I held her breast. Before I could come, she straddled me and lowered herself onto my cock. That night and the next day, she showed me the proper way to fuck her and to lick her pussy and how to satisfy a woman.

I will always treasure that experience which I have put to good use ever since.

(Free Lover 2021 at aol)

(2)  (1)
Anonymous

by Anonymous on Jun 30, 2025 at 4:52 AM

I was 12 my babysitter 16 and hot as hell . Ever since I turned 12 I masturbated daily sometimes several times. I broke my right arm and couldn’t do it with my left. My babysitter came and my mom said I know this is a weird request but can you help him take a shower he just cand do it properly with one hand. I said no problem. I seen him naked befote I have been babysitting for 2 years. It was tin and shit I forgot my bathing suit. I told him I forgot my suit please don’t tell your mother I won’t. I helped him undress and shit his dick was much bigger than I remember. I got the water started covered his cast and he got in. I said I would be in in a minute. I have 36c boobs and my pussy is shaved because I just started having sex with my boyfriend. I got in he said fuck you are so hot. He got rock hard and shit he is bigger than my boyfriend. I washed his back and front then his but and ass crack I was getting horny my nipples were rock hard. Then I cleaned his balls and washed his dick. He asked me to stroke him. He said I beat off twice a day and haven’t been able too and I am bursting. She said ok our little secret. I stood up and stroked him he said ohhh yes and as he was getting close he grabbed my tit and twisted my nipple I came hard as he shot like 10 shots of cum all over me. I got him to bed we had a little talk. He asked me if I was having sex. I said yes. He said do you like it she said I love it. My nipples were hard again in my nightshirt. This kid was turning me on. He said I am hard again. I pulled the covers down my goodness he is rock hard again. I was horny my pussy was soaked. I said you want to have sex. He said fuck yes. I took off my nightshirt and panties. I slowly sank down on his big dick he stretched me then I rode him. His one hand pulling my nipple and twisting it. I was screaming and cumming all over his dick and he lasted a while the second time. Finally he came inside me. I laid with him cleaned his dick with my mouth. And shit he was hard again. He wanted to fuck me but to hard with his arm. I said get out of bed. I went to the edge of the bed so he could fuck me standing up. Boy did he. He fucked me hard I screamed and came so hard he was slapping my tits and twisting my nipples. He came inside me again. His parents came home and all was well. But I missed him. I got a call a month later to babysit. I came in with a sweater but under I had a small halter top on. As soon as the parents left I took it off my tits were on full display. He said you look amazing. Came over and kissed me. Pulled one of my tits out and sucked it . I rubbed his dick it was hard I got in my knees and sucked his dick until he came inside me again my mouth. He said I have been fucking my neighbor and learned something. He pulled down my shorts sat me on the couch and devoured my pussy 10 times better than my boyfriend I came so many times I soaked his face. We went into his bedroom and he fucked me doggie so deep and hard I had multiple orgasms. We fucked for hours. His parents calmed and asked if I could stay they were going to fly to vegas. I said sure. We slept together in the parents bed fucking. We took a shower together and he fucked ne hard from behind. We fucked for the next year .

(0)  (0)

Comment this

Can't read the image? Click here to refresh